Pharmaceutical compositions containing fatty acid amide derivatives

ABSTRACT

A pharmaceutical composition consisting essentially of pharmaceutically effective amount of an N-substituted fatty acid amide of the formula, ##EQU1##  wherein R is a C 13  - C 25  aliphatic hydrocarbon chain or a C 13  - C 25  hydroxylated aliphatic hydrocarbon chain and RCO-- is other than isostearoyl; R&#39; is d- or l-α-C 1  - C 4  alkylbenzyl, racemic-, d- or l-α-C 1  - C 4  alkylbenzyl substituted in the benzene ring with one or two substituents selected from the group consisting of C 1  - C 4  alkyl, C 1  - C 4  alkoxy, halogen and nitro, or racemic-, d- or l-α-benzylbenzyl; R&#34; is hydrogen; or R&#39; and R&#34; together are cyclohexyl; and when RCO-- is isotearoyl R&#39; is alkyl, alkenyl, cycloalkyl, alkylcycloalkyl, hydroxycycloalkyl, alkoxycycloalkyl, alkylphenyl, hydroxyphenyl, alkoxyphenyl, halogenophenyl, halogen-alkyl-substituted phenyl, halogenoalkyl- and halogen-substituted phenyl, alkoxy- and halogen-substituted phenyl, benzyl, racemic-, d- or l-α-C 1  - C 4  alkylbenzyl, benzyl substituted in the benzene ring with lower alkyl or lower alkoxy, racemic-, d- or l-α-benzylbenzyl or hydroxybenzyl, and R&#34; is hydrogen or any one of the groups represented by R&#39;, and a pharmaceutically acceptable carrier, which is useful for lowering elevated levels of cholesterol in the blood.

CROSS REFERENCE TO THE RELATED APPLICATION

This is the divisional application of the U.S. Ser. No. 671,228 filed on Sept. 28, 1967 now abandoned.

The present invention relates to cholesterol-lowering agents. More particularly, it relates to agents which are useful for the lowering of elevated levels of cholesterol in the blood.

Atherosclerosis, which is a form of simple intimal arteriosclerosis, is an adult disease for which there is no known satisfactory cure. Although the cause of atherosclerosis is not yet known, in spite of discussions in the academic world, it has broadly been recognized that one of the most significant histopathological manifestations of atherosclerosis is the deposition of lipids in the blood. Accordingly, research has been directed to the disturbed metabolism of lipids, and attenuation has been given to the extraordinarily elevated level of cholesterol in the blood.

A number of experimental and clinical facts have been reported which indicate the relationship between atherosclerosis and elevated blood cholesterol level. Hence, the development of agents to reduce the elevated blood cholesterol level is extremely important for the prevention of atherosclerosis.

Concentrated efforts have heretofore been made for the development of such agents for lowering cholesterol and a number of compounds have been tested clinically, but none of them have proved to be completely satisfactory. Some are fairly effective but produce harmful side effects which are not negligible, and others have inadequate effectiveness, so that they require to be administered in large doses.

A group of compounds practically employed nowadays for the above purposes comprises unsaturated fatty acids, especially linoleic acid. The reason why linoleic acid is employed is because of its harmlessness to the human body. However, its effectiveness is not very high and it is uncertain and indefinite. Accordingly, large doses are required to obtain at least appreciable efficacy as a cholesterol-lowering agent.

We have found a group of compounds which are effective as cholesterol-lowering agents and are substantially non-toxic.

In accordance with this invention there is provided a cholesterol-lowering agent comprising an N-substituted fatty acid amide having the formula, ##STR1## wherein R is a C₁₃ -C₂₅, branched or straight, saturated or unsaturated, synthetic or natural aliphatic chain having or not having OH group. Examples of RCO are the residues of following fatty acids, in the case of saturated acids, myristic acid, palmitic acid, stearic acid, isostearic acids, arachidic acid, behenic acid, lignoceric acid, cerotic acid and montanic acid; and in the case of unsaturated acids, residues of tsuzuic acid, physetoleic acid, myristoleic acid, zoomaric acid, palmitoleic acid, petroselinic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, erucic acid, brassidic acid, selacholeic acid, linoleic acid, linolenic acid, eleostearic acid, ricinoleic acid, parinaric acid, arachidonic acid, eicosatetraenoic acid. eicosapentaenoic acid, docosapentaenoic acid, hemp-seed oil fatty acid, linseed oil fatty acid, perilla oil fatty acid, styrax oil fatty acid, oiticica oil fatty acid, kayo oil fatty acid, walnut oil fatty acid, poppy-seed oil fatty acid, safflower oil fatty acid, water melon-seed oil fatty acid, soybean oil fatty acid, sunflower oil fatty acid, rice bran oil fatty acid, pumpkin-seed oil fatty acid, kaoliang oil fatty acid, sesame oil fatty acid, corn oil fatty acid, rape oil fatty acid, cottonseed oil fatty acid, olive oil fatty acid, cashew oil fatty acid, tsubaki oil fatty acid, ergot oil fatty acid, castor oil fatty acid, peanut oil fatty acid, palm oil fatty acid, palm kernel oil fatty acid, coconut oil fatty acid, beef tallow fatty acid, lard fatty acid, bone oil fatty acid, horse fat fatty acid, locust oil fatty acid, crystalis oil fatty acid, shark oil fatty acid, cuttlefish oil fatty acid, sardine oil fatty acid, horse-mackerel oil fatty acid, mackerel oil fatty acid, saury pike oil fatty acid, herring oil fatty acid, saurel oil fatty acid, cod oil fatty acid, trout oil fatty acid, gray mullet oil fatty acid, tunny oil fatty acid, menuke oil fatty acid, menhaden oil fatty acid, flatfish oil fatty acid, eel oil fatty acid, various kinds of whale oil fatty acid, body oil fatty acid, skin oil fatty acid, head oil fatty acid, liver oil fatty acid, residual oil fatty acid and egg oil fatty acid and the like plant, land or marine animal oils. In addition on thereto, double bond position isomers or stereoisomers thereof may also be used.

Of the above acids, if desired, saturated fatty acid can be removed roughly from the natural fatty acids according to a suitable method such as, for example, cooling method, urea method, recrystallization method, metal salt method, distillation method and the like.

Further, in the above formula, R' is a d- or l-α-lower alkylbenzyl group, a racemic, d- or l-α-substituted lower alkylbenzyl group having substituents on the benzene ring such as lower alkyl group, halogen atom, lower alkoxy group or nitro group, a racemic, d- or l-α-benzylbenzyl group or adamantyl group, R" is a hydrogen atom or R' and R" are cyclohexyl group, in the case which RCO is an isostearoyl group, R' represents, in addition to the above, an alkyl, alkenyl, cycloalkyl, alkylcycloalkyl, hydroxycycloalkyl, alkoxycycloalkyl, alkylaryl, hydroxyaryl, alkoxyaryl, halogenoaryl, halogenoalkylaryl, halogenoalkyl-halogenoaryl, alkoxyhalogenoaryl, aralkyl, alkylaralkyl, hydroxyaralkyl, alkoxyaralkyl or rac-α-lower alkylaralkyl; and R" is a hydrogen atom, any one of the groups represented by R', or a heterocyclic ring group (having 7 or less carbon atoms) which is constituted by NR'R" containing or not containing oxygen atom.

The starting amines are d- or l-optical isomers of α-lower alkylbenzylamines such as d- or l-α-methylbenzylamine, d- or l-α-ethylbenzylamine, d- or l-α-propyl (n- or i-) benzylamine and d- or l-α-butyl (n-, i- or t-) benzylamine groups, and such racemi, d- or l-amines as α-lower alkylbenzylamine derivatives substituted in the α-position by a lower alkyl group such as a methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl group, and also having radicals in phenyl radical such as one or more members of halogen atoms such as fluorine, chlorine, bromine and iodine atoms, lower alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and t-butyl groups; lower alkoxy groups such as methoxy, ethoxy, n-propoxy, i-apropoxy, n-butoxy, i-butoxy and t-butoxy; and NO₂ radical. These optically active amines can be easily resolved, by the method described in, for example, "Journal of the Chemical Education," Vol. 42, page 296, from racemic amines synthesized according to the process set forth in, for example, "Bulletin de Societe Chimie de Belgiuml" Vol. 72 pages 195-207. Further, rac-, d- and l-α-benzylbenzylamines can be readily resolved according to the process disclosed in "J. Prackt. Chem.," [2] 101, 297 (1921).

In addition thereto, dicyclohexylamines and adamantylamines may also be used.

In the case of isostearoyl amides, there are used, in addition to the above-mentioned amines, mono- or di-alkylamins such as mono- or di-methylamine, mono- or di-ethylamine, mono- or di-n-propylamine, mono- or di-i-propylamine, mono- or di-n-butylamine, mono- or di-i-butylamine, mono- or di-t-butylamine, mono- or di-dodecylamine, mono- or di-palmitylamine, mono- or di-stearylamine, and the like, the mono- or di-alkenylamines such as mono- or di-acrylamine, mono- or di-arylamine, mono- or di-crotonylamine, mono- or di-oleylamine, mono- or di-lineoleylamine, mono- or di-linoleylamine, and the like. Cycloalkylamines such as mono- or di-cyclopentylamine, cyclohexylamine and mono- or dicycloheptylamine, and said cycloalkylamines substituted by one or more members of lower alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and t-butyl; hydroxyl groups; lower alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy and t-butoxy groups; and N-substituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and t-butyl groups. Aromatic amines such as diphenylamines or aniline substituted by one or more members of hydroxyl groups; alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and t-butyl; halogen atoms such as chlorine, fluorine, bromine and iodine atoms; CF₃ ; and alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy and t-butoxy groups. Anilines substituted by lower alkyl groups such as N-methyl, N-ethyl, N-n-propyl, N-i-propyl, N-n-butyl, N-i-butyl and N-t-butyl. Substituted arylamine comprising N-lower alkylanilines substituted by the above-mentioned substituents. Heterocyclic amines such as pyrrole, pyrrolidine, morpholine, piperidine and hexamethyleneimine. Such amines as benzylamine and dibenzylamine or said amines substituted by one or more members of hydroxyl groups, lower alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and t-butyl; alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy and t-butoxy groups; α-substituted lower alkyl groups such as racemic α-methyl, α-ethyl, α-n-propyl, α-i-propyl, α-n-butyl, α-i-butyl and α-t-butyl groups; and N-substituted lower alkyl groups such as N-methyl, N-ethyl, N-n-propyl, N-i-propyl, N-n-butyl, N-i-butyl and N-t-butyl groups.

In the present invention, the isostearic acids signify stearic acids having side chains such as 3-, 4-, 5- to 16-methylheptadecanoic acids. However, these acids and other C₁₈ acids having side chains should be included in the present invention. These substances are free from double bonds and hence have such advantages that they are relatively unsusceptible to oxidation.

For the production of the present N-substituted acid amides may be used any of the processes known for the preparation of acid amides.

For example, (1) a fatty acid of the formula, is made RCOOH to react directly with an amine of the formula, ##STR2## in the presence or absence of such dehydrating agent as a di-substituted carbodiimide compound, p-toluenesulfonic acid or p-toluenesulfonyl chloride or the like in an aqueous or organic solvent, (2) a fatty acid of the formula, RCOOH is converted to acid halide of the formula, RCOX, wherein X is a halogen atom, (Organic Synthesis Vol. 37, page 56) and the resulting acid chloride is brought into contact with at least an equimolar amount of the amine of the formula ##STR3## in the presence of a basic condensing agent, (3) a lower alkyl ester or glyceride of a fatty acid of the formula, ROOCH is made to react directly with the amine of the formula, ##STR4## in the presence or absence of a solvent and condensing agent or (4) a mixed acid anhydride of a fatty acid of the formula, RCOOH, having the formula, ##STR5## wherein R'" is an alkyl or hologenoalkyl having 1 to 4 carbons, is made to react with the amine of the formula, ##STR6## in the presence of a basic condensing catalyst, in the above (1) to (4) processes the R, R' and R" are the same meanings as defined before. The processes (1) to (4) will be more fully explained below. (1) (a) There have already been various researches wherein dicyclohexyl carbodiimide is used in synthesizing polypeptide. But there has never been a report that an amide is synthesized by using such higher fatty acid to produce an antiatherosclerosis agent, and therefore the process of the present invention is significant. Especially, the process of the present invention can be said to be very advantageous because of the fact that the desired product is readily isolated by filtering and separating the urea precipitated when the reaction has been completed, without any special operation and that the said urea can be used again after being regenerated by such treatment as dehydration.

For the di-substituted carbodiimide to be used in the process of the present invention, there may be exemplified dicyclohexylcarbodiimide, diisopropylcarbodiimide, diphenylcarbodiimide and any other dialkyl-, dicyclalkyl- or di-substituted phenyl-carbodiimide. Any of them is equally useful in the process of the present invention.

In carrying out the process, a fatty acid, a corresponding amine and di-substituted carbodiimide, for example, are separately dissolved in an organic solvent, for example, such aromatic hydrocarbon organic solvent as benzene or toluene, such hydrocarbon solvent as n-hexane, cycloalkane, petroleum ether or gasoline, such ether solvent as dioxane, ether or tetrahydrofuran or such alkyl halide solvent as chloroform, ethylene dichloride or carbon tetrachloride or such ester solvent as methyl, ethyl, propyl or butylacetate. These solutions are mixed at once at the room temperature or under cooling when heat generation is severe so as to be of about 1 in the mole ratio, and the mixture is stirred as required and is then allowed to stand at room temperature for about 3 to 24 hours, whereupon the corresponding urea which is a by-product of the reaction will be precipitated. After the precipitates are filtered off, the desired product will be able to be obtained from the filtrate. Further, the excess di-substituted carbodiimide may be decomposed with acetic acid or the like as required.

The recovered urea is dehydrated and the resulting carbodiimide is usable again for the main reaction.

(b) The above-mentioned fatty acid and amine are dissolved in a suitable solvent such as, benzene, toluene, xylene, chloroform or carbon tetrachloride and the like. To the solution is added sulfuric acid, phenolsulfonic acid, p-toluenesulfonic acid, p-toluenesulfonylchloride, or an acidic or basic ion-exchange resin, e.g. IRA-400, IR-50 or IR-120 or Amberlist 15, 21, 26 or 27 as a dehydrating agent. Subsequently, the solution is heated using a water separator to separate and remove the water generated. Thereafter, the solvent is removed and the resultant is purified, whereby a desired product can be obtained in a high yield and in a simple manner. Alternatively, the desired object of the present process may sufficiently be achieved by merely heating the solution in the presence of a dehydrating agent, using as the solvent a tertiary oganic amine such as pyridine, picoline or lutidine, besides the above-mentioned solvent.

c. Thermal dehydration process:

The aforesaid fatty acid and amine are heated at about 130°-300° C. for several hours to several 10 hours, if necessary in the presence of an acid catalyst such as boric acid, whereby a desired product is obtained. In this case, water generated may be removed out of the reaction system or the reaction can be carried out in an autoclave to maintain the higher temperature.

2. The reaction for condensing an organic amine with an acid halide is also known. However, so far as we know, there has been no report on the production of antiatherosclerosis agents by utilizing this process. We have found that, by using this process, an amide derivative which is useful as an antiatherosclerosis agent can be obtained at a favorable yield under a mild nonoxidative condition.

Even when an excess of such basic condensing agent as such caustic alkali as caustic lithium soda or potash, such alkaline earth hydroxide as calcium or barium hydroxide, such alkali carbonate as lithium, sodium or potassium carbonate, such alkaline earth carbonate as calcium or barium carbonate, such tertiary amine as trimethylamine, triethylamine dimethylaniline, pyridine, picoline, anion exchange resin or an excess of the starting amine or any of the above-mentioned amines is used, the object of the invention will be able to be attained.

As for the solvent in this reaction, is used water, such organic ketone as acetone, methylethyl ketone or methylisobutyl ketone, such ester as methyl acetate, ethyl acetate, propyl acetate or butyl acetate, such other as ethyl ether, propyl ether, tetrahydrofuran or dioxane, such hydrocarbon solvent as n-hexane, cyclohexane, benzene or toluene, such alkyl halide as ethylene dichloride, chloroform or carbon tetrachloride, such as tertiary amine as dimethyl formamide, pyridine or picoline or any of the starting material amines as alone or as properly mixed.

Any temperature from the freezing point up to near the boiling point of the solvent used can be applied to the reaction. Further, it is desirable that the reaction is conducted in a stream of such inert gas as nitrogen or helium.

3. a. Process using glycerides:

The aforesaid oil glyceride and an equimolar amount of an amine are mixed with a basic catalyst such as, sodium methylate, soldium ethylate, potassium butylate, potassium hydroxide or sodium hydroxide and the like, or with an acidic catalyst such as ammonium chloride or boric acid and the like, and the mixture is heated at about 50° - 300° C. for 30 minutes to several ten hours to obtain a desired product. Even in the absence of the basic or acidic catalyst, the desired product can be obtained in a favorable yield when the amine is used in excess. In this case, the object can be achieved either in the presence or absence of an inert organic solvent.

b. Process using esters:

An ester of the aforesaid fatty acid or of a fatty acid mixture obtained from the aforesaid oils or fats is mixed with an amine, and the mixture is heated at about 100° - 300° C. for 30 minutes to several 10 hours either in the presence or absence of the above-mentioned basic or acidic catalyst and of an inert organic solvent, whereby the object of the present process can be achieved. In this case, an alcohol formed may be removed out of the reaction system or an autoclave may be used.

The reactions of both processes (a) and (b) mentioned above should be done in an inert gas such as nitrogen to inhibit the formation of peroxides, coloring matters and the like undesirable by-products.

4. The reaction of mixed anhydride method which is carried out at a low temperature is substantially complete at a low temperature is substantially complete at about 0° C. Unsaturated fatty acid derivatives, in particular, are unstable substances which, under certain conditions undergo oxidation, polymerization, position or geometrical isomerization and the like due to heat and air. Therefore, the process for producing unsaturated fatty acid amide derivatives according to the present invention, which is a low temperature reaction, has found a great significance to attain excellent results.

The solvents employed in the present reaction include ether, dioxane, tetrahydrofuran, dichloromethane, chloroform, carbon, tetrachloride, methyl acetate, ethyl acetate, benzene, toluene, xylene, acetone and methylisobutylketone. As the basic materials, organic solvent-soluble tertiary amines such as trimethylamine, triethylamine, dimethylaniline, diethylaniline and pyridine and the like are desirably used. In some cases, however, inorganic bases, such as potassium carbonate and sodium carbonate, or basic ion exchange resins may also be used.

In order to prepare said mixed acid having 1 to 4 carbon atoms ester is reacted with a fatty acid of the formula, RCOOH wherein R is the same meanings as identified above. Examples of the said lower alkyl halogeno acid ester include chloroformate, and acetate.

The chloroformate, and acetate to be employed are methyl chloroformate, acetate, ethyl chloroformate, acetate and butyl chloroformate, acetate and the like.

The effectiveness of the compounds was tested by using mice fed on a specific diet which was enriched with cholesterol and bile acids. The blood cholesterol level of the mice had been raised to 3 to 6 times as high as the normal level. The amide compound as well was mixed with the specific diet in an amount of 0.2%, and continuously administered orally for 8 to 12 days. Then the total cholesterol value in the blood serum of the animals was evaluated. During the tests, unfavourable side effects, such as the prevention of body weight gain and others, were not observed. It is noted that the stated compound is superior to linoleic acid. Moreover, in the linoleic acid-administered group, ineffective cases were sometimes observed due to the individual difference of the animals, and the effectiveness varied considerably even in the same individual animal. While, it should be emphasized that no such phenomena were observed in the acidamide administered group.

Another significant effect of the N-substituted acidamide compounds according to the present invention is to prevent the deposition of cholesterol and fat in the liver, which occurs in animals fed on a diet rich in cholesterol. It seems that the linoleamide compounds improve the declined lipid-metabolism function of the liver. This effectiveness is also favorable, in view of the fact that the metabolism of lipid mainly relies upon the function of the liver. In the administration of linoleic acid, such effectiveness is never observed. The results are shown in Table 1.

The extremely low toxicities of the present acid-amide compounds are illustrated in Table 2, in which the acute toxicities of some of the present compounds in mice are listed.

                                      Table 1                                      __________________________________________________________________________                                  Serum Liver                                                                    cholesterol                                                                          cholesterol                                         Compound             mg %  mg/100 g.                                   __________________________________________________________________________     [I] Control (no compound added)                                                                             546   3585                                            Linoleic acid            324   4585                                            (+) N-(α-Methylbenzyl)-linoleamide                                                                267   764                                             (+) N-(α-Methylbenzyl)-oleamide                                                                   288   797                                             (+) N-(α-Methylbenzyl)-linolenamide                                                               269   784                                             (+) N-(α-Methylbenzyl)-isostearamide                                                              251   761                                             Safflower oil (+)α-methylbenzylamide                                                              273   790                                             Soybean oil (+)α-methylbenzylamide                                                                280   805                                             Linseed oil (+)α-methylbenzylamide                                                                291   796                                             Cod oil (+)α-methylbenzylamide                                                                    251   743                                             Cuttlefish oil (+)α-ethylbenzylamide                                                              248   748                                             Cotton seed oil (+)α-propylbenzylamide                                                            262   800                                         [II]                                                                               Control (no compound added)                                                                             521   3308                                            Linoleic acid            329   4491                                            (-) (α-Methylbenzyl)-linoleamide                                                                  286   908                                             (-) (α-Methylbenzyl)-oleamide                                                                     283   808                                             (-) (α-Methylbenzyl)-linolenamide                                                                 253   767                                             (-) (α-Methylbenzyl)-isostearamide                                                                246   777                                             (-) (α-Ethylbenzyl)-linoleamide                                                                   251   821                                               Safflower oil (-)α-methylbenzylamide                                                            276   898                                               Soybean oil (-)α-methylbenzylamide                                                              274   799                                               Linseed oil (-)α-methylbenzylamide                                                              290   776                                                Sardine oil (-)α-methylbenzylamide                                                             261   744                                               Cod oil (-)α-methylbenzylamide                                                                  250   739                                              ##STR7##                290   815                                              ##STR8##                295   1330                                             ##STR9##                302   1620                                             ##STR10##               252   1820                                             ##STR11##               300   906                                              ##STR12##               314   1160                                             ##STR13##               274   992                                              ##STR14##               302   1042                                             ##STR15##               290   992                                              ##STR16##               277   968                                         [III]                                                                              Control (no compound added)                                                                             471                                                    ##STR17##               225   946                                              ##STR18##               315   856                                              ##STR19##               385   1511                                             ##STR20##               322   1341                                             ##STR21##               242   1065                                             ##STR22##               237   1047                                        [IV]                                                                               Control (no compound added)                                                                             595   3145                                             ##STR23##               240   828                                              ##STR24##               321   908                                              ##STR25##               217   826                                              ##STR26##               251   1000                                             ##STR27##               234   1007                                             ##STR28##               297   905                                              ##STR29##               222   913                                              ##STR30##               216   1003                                             ##STR31##               232   922                                         [V] Control (no compound added)                                                                             372   2640                                            Linoleic acid            351   3124                                                       ##STR32##     238   729                                         C.sub.17 H.sub.31 CO                                                                         "              214   544                                         d-            "              200   500                                         l-            "              208   623                                                        ##STR33##     245   831                                         d-            "              222   729                                         l-            "              263   888                                         iso-C.sub.17 H.sub.35 CO                                                                     "              221   609                                         d-            "              209   561                                         l-            "              252   639                                         Safflower oil-CO                                                                             "              220   575                                         d-            "              204   515                                         l-            "              253   632                                         Linseed oil-CO                                                                               "              249   800                                         Cuttlefish-oil-CO                                                                            "              223   631                                         Shark oil-CO  "              248   621                                         Sardine oil-CO                                                                               "              231   607                                         [VI]                                                                                ##STR34##                                                                                ##STR35##     508 314  260  261 266 278 249 258 269                                                3270  4550  784 1071  821 1081  920                                            830 1005                                    [VII]                                                                              Control (no compound added)                                                                             508   3535                                            Linoleic acid            341   4550                                             ##STR36##               278   1081                                             ##STR37##               281   1053                                             ##STR38##               265   1061                                             ##STR39##               232   868                                              ##STR40##               290   1100                                             ##STR41##               300   1090                                        [VIII]                                                                             Control (no compound added)                                                                             472   2652                                             ##STR42##               299   1003                                             ##STR43##               287   992                                              ##STR44##               340   1603                                             ##STR45##               331   980                                              ##STR46##               294   821                                              ##STR47##               362   1305                                             ##STR48##               300   1091                                             ##STR49##               309   1113                                             ##STR50##               312   982                                              ##STR51##               300   1502                                             ##STR52##               340   1403                                        [IX]                                                                               Control (no compound added)                                                                             336   2200                                             ##STR53##               288   721                                              ##STR54##               294   1120                                             ##STR55##               279   750                                              ##STR56##               280   761                                              ##STR57##               292   745                                              ##STR58##               300   802                                              ##STR59##               270   777                                              ##STR60##               259   758                                         [X] Control                  554   3293                                             ##STR61##               228   820                                              ##STR62##               304   1010                                             ##STR63##               398   1210                                             ##STR64##               254   841                                              ##STR65##               308   923                                              ##STR66##               249   1000                                             ##STR67##               295   1015                                             ##STR68##               230   841                                              ##STR69##               299   1014                                             ##STR70##               262   823                                              ##STR71##               315   1022                                        [XI]                                                                               Control                  595   3451                                             ##STR72##               230   845                                              ##STR73##               275   1011                                             ##STR74##               315   1098                                             ##STR75##               325   1061                                             ##STR76##               352   1125                                             ##STR77##               299   1039                                             ##STR78##               253   921                                              ##STR79##               277   1009                                             ##STR80##               362   1342                                             ##STR81##               289   906                                              ##STR82##               315   1125                                             ##STR83##               382   1210                                             ##STR84##               306   1069                                             ##STR85##               318   1115                                             ##STR86##               309   929                                              ##STR87##               299   1068                                             ##STR88##               239   906                                              ##STR89##               256   929                                              ##STR90##               321   1222                                             ##STR91##               367   1191                                             ##STR92##               300   949                                              ##STR93##               333   1094                                             ##STR94##               309   1125                                             ##STR95##               275   995                                              ##STR96##               300   1029                                             ##STR97##               245   1004                                             ##STR98##               365   1325                                             ##STR99##               240   623                                              ##STR100##              275   1632                                             ##STR101##              325   1450                                             ##STR102##              280   870                                              ##STR103##              339   1620                                             ##STR104##              350   1062                                             ##STR105##              255   823                                              ##STR106##              372   1234                                             ##STR107##              270   985                                              ##STR108##              291   1109                                             ##STR109##              378   1229                                             ##STR110##              388   1411                                             ##STR111##              300   974                                              ##STR112##              365   889                                              ##STR113##              290   714                                              ##STR114##              323   1158                                             ##STR115##              275   967                                              ##STR116##              339   1450                                             ##STR117##              222   711                                              ##STR118##              320   1069                                             ##STR119##              340   1215                                             ##STR120##              279   887                                              ##STR121##              350   1309                                                                     Blood cholesterol                                                              level index                                       [XII]                        %                                                     Control                  100                                                    ##STR122##              62                                                10  iso-NHCH.sub.2 CHCH.sub.2                                                                               58                                                     ##STR123##                                                                     ##STR124##              60                                                     ##STR125##              72                                                     ##STR126##              54                                                     ##STR127##              71                                                     ##STR128##              68                                                     ##STR129##              42                                                     ##STR130##              55                                                     ##STR131##              63                                                     ##STR132##              62                                                     ##STR133##              60                                                     ##STR134##              58                                                     ##STR135##              44                                                __________________________________________________________________________

                  Table 2                                                          ______________________________________                                         LD.sub.50 (Mouse, P.O.)                                                        ______________________________________                                          ##STR136##          > 50 g/kg                                                  ##STR137##          > 50 g/kg                                                  ##STR138##          > 50 g/kg                                                  ##STR139##          > 50 g/kg                                                  ##STR140##          > 50 g/kg                                                  ##STR141##          > 50 g/kg                                                  ##STR142##          > 50 g/kg                                                  ##STR143##          > 50 g/kg                                                 ______________________________________                                    

Further, the present compounds were administered to rabbits in a dose of 200 mg/day together with a cholesterol rich diet to obtain such favorable results as shown below. Serum cholesterol, mg. %.

    __________________________________________________________________________     Compound 2 weeks                                                                             4 weeks                                                                             6 weeks                                                                             8 weeks                                                                             10 weeks                                          __________________________________________________________________________     Control  250  563  890  1150 1750                                              β-Sitosterol                                                                       250  438  875  1063 1200                                              N,N-dicyclohexyl                                                                        250  120   62   62   65                                               linoleamide                                                                     ##STR144##                                                                             250  130   65   60   52                                                                            Rabbit serum cholesterol                                                       Towering ratio                                    Compound            Dose     (after 9 weeks)                                   __________________________________________________________________________     Control             0        0%                                                β-Sitosterol   800 mg/kg/day                                                                           21.2%                                              ##STR145##         100 mg/kg/day                                                                           60.1%                                              ##STR146##         100 mg/kg/day                                                                           59.2%                                              ##STR147##         100 mg/kg/day                                                                           80.1%                                              ##STR148##         100 mg/kg/day                                                                           61.5%                                              ##STR149##         100/mg/day                                                                              58.3%                                              ##STR150##         100 mg/kg/day                                                                           59.4%                                              ##STR151##         100 mg/kg/day                                                                           54.5%                                              ##STR152##         100 mg/kg/day                                                                           60.6%                                              ##STR153##         100 mg/kg/day                                                                           67.3%                                             __________________________________________________________________________

All the products involved in the present invention are novel compounds unknown to the literature.

As is seen from Table 2, no fatal case and no significant toxic symptoms were observed even in such large doses (per os) as 0.5 g. per 10 g., namely 50 g./kg. of the body weight. Also, no significant toxic symptoms, or fatal cases, were observed when the amides in amounts of 1, 0.5 or 0.2% in the diet were administered to mice everyday for three weeks. The appetite was normal and digestive functions were unchanged. When the internal organs were inspected by dissection, there was no appreciable change.

The cholesterol-lowering agents of this invention may be orally administered. Usually the amount orally administered is 0.1 g. -20 g. per day, preferably 0.5 g. -5 g. per day and the administration may be continued for 1 to 5 months, usually for 3 months. The cholesterol-lowering agent may be in any suitable form which is conventional for oral administration. Thus, it may be encased in a capsule, or it may be in a liquid form, in a tablet form, or in a powder form. In preparing the agents in these various forms, the active compound may be mixed with or impregnated in a suitable solid carrier, or it may be mixed with a liquid carrier such as an edible oil, preferably those containing linoleic acid. It is also possible to use a mixture of two or more of the N-substituted amides of the invention. It may also be used as mixed with linoleic acid.

The present invention will be explained in detail with reference to the following examples which are given only for illustration and not for limitation of the invention in any way.

EXAMPLE 1

A mixture of 10 g. of linoleic acid and 5 g. of l(-)α-methylbenzylamine was heated and refluxed for about 8 hours in 300 ml. of toluene in the presence of 0.2 g. of p-toluenesulfonic acid, while using a water separator.

After completion of the reaction, the toluene layer formed was subjected to acid-washing, alkali-washing and water-washing, was dried and was then concentrated to obtain 12.3 g. of a desired product, m.p. 200°-221° C./0.05 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.40          81.70                                               H (%)       10.77          10.88                                               N (%)        3.65           3.48                                               ______________________________________                                    

Examples 2-37 are shown in the following in which:

Dehydration assistant:

A. p-Toluenesulfonic acid.

B. p-Toluenesulfonic acid chloride.

C. sulfuric acid.

D. phenolsulfonic acid.

E. ira-400

f. amberlist-15

Solvent:

a. Toluene

b. Pyridine

c. Benzene

d. Chloroform

e. Xylene

f. Tetrachlorocarbon

    __________________________________________________________________________      ##STR154##                                                                                    Dehyd- Reac-                                                   Exam-           ration tion        C %      H %      N %                       ple             assis-                                                                             Sol-                                                                              time                                                                               b.p.    Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-               No. Fatty acid                                                                             --R""                                                                              tant                                                                               vent                                                                              (hr)                                                                               ° C./mmHg                                                                       tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical                __________________________________________________________________________      2  Oleic acid                                                                             CH.sub.3                                                                           A   a  8   203-214/0.05                                                                           80.98                                                                               81.22                                                                              11.24                                                                               11.46                                                                              3.63 3.44                  3  Oleic acid                                                                             CH.sub.3                                                                           B   b  20  204-218/0.07                                                                           80.98                                                                               81.10                                                                              11.24                                                                               11.42                                                                              3.63 3.43                  4  Linoleic acid                                                                          CH.sub.3                                                                           A   d  10  200-217/0.05                                                                           81.40                                                                               81.65                                                                              10.77                                                                               10.90                                                                              3.65 3.41                  5  Linoleic acid                                                                          CH.sub.3                                                                           D   e  10  202-218/0.05                                                                           81.40                                                                               81.65                                                                              10.77                                                                               10.90                                                                              3.65 3.42                  6  Linolenic acid                                                                         CH.sub.3                                                                           A   a  10  204-213/0.05                                                                           81.83                                                                               82.00                                                                              10.30                                                                               10.62                                                                              3.67 6.32                  7  Linolenic acid                                                                         CH.sub.3                                                                           E   e  10  206-214/0.05                                                                           81.83                                                                               82.13                                                                              10.30                                                                               10.54                                                                              3.67 6.45                  8  Isostearic acid                                                                        CH.sub.3                                                                           A   f  12  206-217/0.04                                                                           80.56                                                                               80.70                                                                              11.70                                                                               11.75                                                                              3.61 3.58                  9  Isostearic acid                                                                        CH.sub.3                                                                           B   b  20  202-218/0.06                                                                           80.56                                                                               80.70                                                                              11.70                                                                               11.97                                                                              3.61 3.46                 10  Safflower oil                                                                          C.sub.2 H.sub.5                                                                    F   e  8   205-217/0.06                                        11  Soybean oil                                                                            CH.sub.3                                                                           A   e  8   204-216/0.05                                        12  Sesame oil                                                                             CH.sub.3                                                                           A   e  8   200-218/0.06                                        13  Castor oil                                                                             CH.sub.3                                                                           A   d  8   196-216/0.05                                        14  Corn oil                                                                               C.sub.2 H.sub.5                                                                    B   b  20  186-218/0.05                                        15  Cottonseed oil                                                                         CH.sub.3                                                                           A   f   8  189-208/0.06                                        16  Olive oil                                                                              CH.sub.3                                                                           D   a   8  183-207/0.05                                        17  Linseed oil                                                                            CH.sub.3                                                                           C   a  10  187-212/0.05                                        18  Rape seed oil                                                                          CH.sub.3                                                                           A   a  12  193-214/0.06                                        19  Rice bran oil                                                                          CH.sub.3                                                                           A   a   8  193-218/0.05                                        20  Chrysalis oil                                                                          CH.sub.3                                                                           C   a   8  188-212/0.06                                        21  Sunflower oil                                                                          CH.sub.3                                                                           A   e   8  191-215/0.06                                        22  Flatfish oil                                                                           CH.sub.3                                                                           D   e   8  196-220/0.05                                        23  Shark oil                                                                              CH.sub.3                                                                           A   a  10  186-209/0.06                                        24  Whale oil                                                                              CH.sub.3                                                                           E   a  10  184-220/0.05                                        25  Cuttlefish oil                                                                         CH.sub.3                                                                           A   a   8  198-219/0.06                                        26  Sardine oil                                                                            CH.sub.3                                                                           B   b  20  201-218/0.06                                        27  Mackerel oil                                                                           CH.sub.3                                                                           F   a   8  200-217/0.05                                        28  Saury pike oil                                                                         C.sub.2 H.sub.5                                                                    A   c   8  187-216/0.06                                        29  Herring oil                                                                            CH.sub.3                                                                           C   d  10  186-215/0.05                                        30  Saurel oil                                                                             CH.sub.3                                                                           A   a  10  184-213/0.05                                        31  Manhaden oil                                                                           CH.sub.3                                                                           A   a  10  182-222/0.08                                        32  Cod oil CH.sub.3                                                                           A   e   8  192-218/0.05                                        33  Liver oil                                                                              CH.sub.3                                                                           D   f  12  182-217/0.06                                        34  Residual oil                                                                           CH.sub.3                                                                           A   a  8   184-223/0.08                                        35  Manuke oil                                                                             CH.sub.3                                                                           A   e  8   176-226/0.08                                        36  Safflower oil                                                                          C.sub.3 H.sub.7                                                                    A   e  10  199-204/0.02                                        37  Safflower oil                                                                          C.sub.4 H.sub.9                                                                    A   e  10  197-209/0.03                                        __________________________________________________________________________

EXAMPLE 38

Linoleic acid (10 g.), 5 g. of (-)α-methylbenzylamine and 10 g. of dicyclohexyl carbodiimide were individually dissolved in 50 ml. of toluene. The solutions were mixed together at one portion, and the mixed solution was allowed to stand at room temperature for 8 hours.

After filtering the solution, the filtrate was with acid, alkali and water, and was then dried, concentrated and distilled to obtain 11.1 g. of a desired product, b.p. 201°-209° C./0.04 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical Analytical                                               ______________________________________                                         C (%)       81.40         81.51                                                H (%)       10.77         10.88                                                N (%)        3.65          3.51                                                ______________________________________                                    

Examples 39-74 are shown in the table below.

    __________________________________________________________________________                                         C %      H %      N %                      Example      Amine                                                                             BNCNB       b.p.    Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-              No.  Acid    R""                                                                               B     Solvent                                                                              ° c./mmHg                                                                       tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical               __________________________________________________________________________     39   Linoleic acid                                                                          CH.sub.3                                                                           ##STR155##                                                                          Ether 200-208/0.04                                                                           81.40                                                                               81.77                                                                              10.77                                                                               10.73                                                                              3.65 3.45                40   Linoleic acid                                                                          CH.sub.3                                                                           ##STR156##                                                                          Dioxane                                                                              204-208/0.04                                                                           81.40                                                                               81.65                                                                              10.79                                                                               10.91                                                                              3.65 3.38                41   Oleic acid                                                                             CH.sub.3                                                                           ##STR157##                                                                          Dioxane                                                                              203-219/0.06                                                                           80.98                                                                               81.03                                                                              11.24                                                                               11.34                                                                              3.63 3.49                42   Linolenic acid                                                                         CH.sub.3                                                                           ##STR158##                                                                          Tetrahydro-  furan                                                                   205-217/0.05                                                                           81.83                                                                               82.06                                                                              10.30                                                                               10.55                                                                              3.67 3.47                43   Isostearic acid                                                                        CH.sub.3                                                                           ##STR159##                                                                          Ether 208-218/0.07                                                                           80.56                                                                               80.71                                                                              11.70                                                                               11.86                                                                              3.61 3.54                44   Isostearic acid                                                                        CH.sub.3                                                                           ##STR160##                                                                          Toluene                                                                              200-214/0.05                                                                           80.56                                                                               80.98                                                                              11.70                                                                               11.87                                                                              3.61 3.48                45   Safflower oil  fatty acid                                                              C.sub.2 H.sub.5                                                                    ##STR161##                                                                          Toluene                                                                              201-214/0.05                                       46   Soybean oil fatty acid                                                                 CH.sub.3                                                                           ##STR162##                                                                          Chloroform                                                                           195-218/0.05                                       47   Sesame oil fatty acid                                                                  CH.sub.3                                                                           ##STR163##                                                                          Toluene                                                                              189-218/0.07                                       48   Castor oil fatty acid                                                                  CH.sub.3                                                                           ##STR164##                                                                          Tetrachloro- carbon                                                                  193-213/0.07                                       49   Rape-seed oil                                                                          CH.sub.3                                                                           ##STR165##                                                                          Benzene                                                  50   Olive oil fatty acid   194-211/0.06 -                                                  C.sub.2 H.sub.5                                                                    ##STR166##                                                                          Pyridine                                                                             196-215/0.06                                       51   Rice bran oil fatty acid                                                               CH.sub.3                                                                           ##STR167##                                                                          Benzene                                                                              185-214/0.06                                       52   Cottonseed oil fatty acid                                                              CH.sub.3                                                                           ##STR168##                                                                          Toluene                                                                              198-218/0.05                                       53   Corn oil fatty acid                                                                    CH.sub.3                                                                           ##STR169##                                                                          Toluene                                                                              199-218/0.05                                       54   Peanut oil fatty acid                                                                  CH.sub.3                                                                           ##STR170##                                                                          Ether 195-218/0.06                                       55   Olive oil fatty acid                                                                   CH.sub.3                                                                           ##STR171##                                                                          Toluene                                                                              191-219/0.06                                       56   Chrysalis oil fatty acid                                                               CH.sub.3                                                                           ##STR172##                                                                          Toluene                                                                              196-215/0.05                                       57   Shark oil fatty acid                                                                   CH.sub.3                                                                           ##STR173##                                                                          Benzene                                                                              205-222/0.05                                       58   Cuttlefish oil fatty acid                                                              CH.sub.3                                                                           ##STR174##                                                                          Toluene                                                                              181-228/0.05                                       59   Sardine oil fatty acid                                                                 CH.sub.3                                                                           ##STR175##                                                                          Ether 192-226/0.07                                       60   Mackerel oil  fatty acid                                                               CH.sub.3                                                                           ##STR176##                                                                          Ether 194-216/0.05                                       61   Saury pike oilfatty acid                                                               CH.sub.3                                                                           ##STR177##                                                                          Benzene                                                                              190-217/0.06                                       62   Herring oil fatty acid                                                                 CH.sub.3                                                                           ##STR178##                                                                          Ether 192-218/0.05                                       63   Saurel oil fatty acid                                                                  CH.sub.3                                                                           ##STR179##                                                                          Toluene                                                                              182-218/0.05                                       64   Cod oil fatty acid                                                                     CH.sub.3                                                                           ##STR180##                                                                          Chloroform                                                                           186-216/0.05                                       65   Trout oil fatty acid                                                                   CH.sub.3                                                                           ##STR181##                                                                          Tetrahydro- furan                                                                    180-219/0.05                                       66   Gray mullet oil fatty acid                                                             CH.sub.3                                                                           ##STR182##                                                                          Tetrahydro- furan                                                                    194-225/0.05                                       67   Menuke oil fatty acid                                                                  CH.sub.3                                                                           ##STR183##                                                                          Toluene                                                                              189-215/0.06                                       68   Menhaden oil fatty acid                                                                C.sub.2 H.sub.5                                                                    ##STR184##                                                                          Dioxane                                                                              193-226/0.05                                       69   Eel oil fatty acid                                                                     CH.sub.3                                                                           ##STR185##                                                                          Benzene                                                                              196-229/0.05                                       70   Flatfish oil fatty acid                                                                CH.sub.3                                                                           ##STR186##                                                                          Dioxane                                                                              189-220/0.05                                       71   Whale oil fatty acid                                                                   CH.sub.3                                                                           ##STR187##                                                                          Benzene                                                                              175-223/0.06                                       72   Liver oil fatty acid                                                                   CH.sub.3                                                                           ##STR188##                                                                          Toluene                                                                              190-218/0.07                                       73   Residual oil fatty acid                                                                C.sub.2 H.sub.5                                                                    ##STR189##                                                                          Toluene                                                                              194-228/0.08                                       74   Safflower oil fatty acid                                                               C.sub.3 H.sub.7                                                                    ##STR190##                                                                          Dioxane                                                                              199-209/0.06                                       __________________________________________________________________________

EXAMPLE 75

A mixture of 10 g. of linoleic acid and 6 g. of l(-)α-methylbenzylamine, was heated at 180° C. for 24 hours removing water out of the reaction system. The reaction mixture was immediately subjected to distillation to obtain 11.3 g. of a desired product, b.p. 203°-221° C./0.07 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.40          81.56                                               H (%)       10.77          10.86                                               N (%)        3.65           3.55                                               ______________________________________                                    

Examples 76-103 are shown in the table below.

    __________________________________________________________________________      ##STR191##                                                                                    Reac-                                                                               Reac-                                                                     tion tion       C %      H %      N %                          Example                                                                             Acid       temper-                                                                             time                                                                               b.p.   Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                  No.  RCOOH   R""                                                                               ature                                                                               (hr)                                                                               ° C./mmHg                                                                      tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical                   __________________________________________________________________________     76   Isostearic acid                                                                        o  180  24  206-218/0.06                                                                          80.56                                                                               80.67                                                                              11.70                                                                               11.98                                                                              3.61 3.38                    77   Oleic acid                                                                             o  180  24  206-217/0.05                                                                          80.98                                                                               81.28                                                                              11.24                                                                               11.53                                                                              3.63 3.39                    78   Linolenic acid                                                                         o  180  24  209-216/0.06                                                                          81.83                                                                               81.95                                                                              10.30                                                                               10.54                                                                              3.67 3.38                    79   Safflower oil                                                                          o  180  24  194-219/0.07                                               acid                                                                      80   Soybean oil acid                                                                       o  200  20  197-221/0.05                                          81   Corn oil acid                                                                          o  180  20  193-208/0.06                                          82   Cottonseed oil                                                                         x  180  24  197-215/0.05                                               acid                                                                      83   Sesame oil acid                                                                        o  160  36  198-206/0.04                                          84   Castor oil acid                                                                        o  160  36  200-222/0.04                                          85   Olive oil acid                                                                         o  180  24  188-211/0.06                                          86   Rape-seed oil                                                                          o  180  24  206-216/0.05                                               acid                                                                      87   Sunflower oil                                                                          o  180  24  198-214/0.06                                               acid                                                                      88   Linseed oil acid                                                                       o  180  24  188-215/0.05                                          89   Rice bran oil                                                                          o  180  24  181-213/0.07                                               acid                                                                      90   Shark oil acid                                                                         x  180  24  185-221/0.05                                          91   Whale oil acid                                                                         o  180  26  175-225/0.04                                          92   Mackerel oil                                                                           o  180  24  193-208/0.06                                               acid                                                                      93   Saurel oil acid                                                                        o  180  24  189-215/0.07                                          94   Cuttlefish oil                                                                         o  200* 18  186-214/0.06                                               acid                                                                      95   Cod oil acid                                                                           o  200* 18  188-222/0.08                                          96   Herring oil acid                                                                       o  210* 18  193-215/0.04                                          97   Sardine oil acid                                                                       o  180  20  196-220/0.08                                          98   Flatfish oil                                                                           o  180  24  194-221/0.05                                               acid                                                                      99   Menhaden oil                                                                           o  180  24  190-218/0.06                                               acid                                                                      100  Liver oil acid                                                                         o  180  20  195-220/0.05                                          101  Residual oil                                                                           o  180  20  186-215/0.05                                               acid                                                                      102  Safflower oil                                                                          +  180  20  202-210/0.04                                               acid                                                                      103  Safflower oil                                                                             180  20  205-211/0.05                                               acid                                                                      __________________________________________________________________________      * In an autoclave                                                              o = CH.sub.3                                                                   x = C.sub.2 H.sub.5                                                            +  = C.sub.3 H.sub.7                                                             = C.sub.4 H.sub.9                                                      

EXAMPLE 104

A mixture of 10 g. of methyl linoleate and 6 g. of (-)α-methylbenzylamine was heated in a nitrogen atmosphere at 180° C. for 30 hours removing methanol out of the reaction system. The reaction mixture was distilled to obtain 12.3 g. of a desired product, b.p. 200°-216° C./0.05 mmHg, [α] D₂₅ -59.5. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.40          81.60                                               H (%)       10.77          10.81                                               N (%)        3.65           3.48                                               ______________________________________                                    

EXAMPLE 105

A mixture of 10 g. of methyl isostearate, 5 g. of (-)α-methylbenzylamine and 1 g. of sodium methylate was heated at 150° C. for 3 hours, while excluding out of the reaction system methanol by-produced in this case. Subsequently, the reaction mixture was washed with acid, alkali and water according to ordinary procedures, and was then dried and concentrated to obtain 12.3 g. of a desired product, b.p. 205°-226° C./0.06 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.56          80.50                                               H (%)       11.70          11.78                                               N (%)        3.61           3.74                                               ______________________________________                                    

EXAMPLE 106

To a mixture comprising 10 g. of ethyl oleate and 5 g. of (-)α-methylbenzylamine was added a solution of 0.5 g. of sodium in 8 ml. of ethyl alcohol. The mixture was reacted at 160° C. for about 2 hours removing ethyl alcohol during reaction. Thereafter, the same treatments as in Example 2 were effected to obtain 12.0 g. of a desired product, b.p. 208°-218° C./0.06 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.98          80.89                                               H (%)       11.24          11.18                                               N (%)        3.63           3.80                                               ______________________________________                                    

EXAMPLE 107

A mixture of 10 g. of safflower oil and 6 g. of (-)α-methylbenzylamine was heated in an autoclave at 200° C. for 12 hours and was then immediately distilled to obtain 13.0 g. of a desired product, b.p. 197°-226° C./0.05 mmHg.

Examples 108-139 are shown in the following table:

    __________________________________________________________________________      ##STR192##                                                                                      Refer-                                                                             Reac-                                                                               Reac-                                                                 ence                                                                               tion tion                                                Example                                                                             Ester or     exam-                                                                              temper-                                                                             time                                                                               Cata-                                                                               Sol-                                                                               b.p.                                   No.  glyceride R""                                                                               ple ature                                                                               (h) lyst vent                                                                               ° C./mmHg                       __________________________________________________________________________     108  Methyl linoleate                                                                         o  4   200  12           200-214/0.04                           109  Ethyl linoleate                                                                          o  1   180  48           203-209/0.05                           110  Methyl oleate                                                                            o  2   160   4  KOtBu    204-227/0.06                           111  Methyl isostearate                                                                       o  3   160   2  NaOCH.sub.3,                                                                        CH.sub.3 OH                                                                        206-218/0.07                           112  Methyl linolenate                                                                        o  4   200  14           206-218/0.05                           113  Safflower oil                                                                            o  4   200  14           198-209/0.05                                methyl ester                                                              114  Sesame oil methyl                                                                        o  4   200  12           198-213/0.05                                esters                                                                    115  Castor oil methyl                                                                        o  1   180  42           199-218/0.05                                ester                                                                     116  Rape-seed oil                                                                            *  1   180  40           188-209/0.05                                methyl ester                                                              117  Olive oil methyl                                                                         o  2   150   3  NaOCH.sub.3                                                                             188-209/0.05                                ester                                                                     118  Rica bran oil                                                                            o  4   180  10           189-214/0.15                                methyl ester                                                              119  Cottonseed oil                                                                           *  1   180  38           195-203/0.05                                methyl ester                                                              120  Chrysalis oil methyl                                                                     o  1   180  38           193-216/0.06                                ester                                                                     121  Sardine oil methyl                                                                       o  1   180  42           187-218/0.05                                ester                                                                     122  Fish oil methyl                                                                          o  1   180  42           187-212/0.05                                ester                                                                     123  Flatfish oil methyl                                                                      o  1   180  38           197-224/0.05                                ester                                                                     124  Safflower oil                                                                            *  4   190  20           199-215/0.05                           125  Linseed oil                                                                              o  4   190  18           187-214/0.06                           126  Soybean oil                                                                              o  4   190  18           195-218/0.06                           127  Sunflower oil                                                                            o  4   200  12           196-212/0.06                           128  Corn oil  o  4   200  12           195-218/0.07                           129  Shark oil o  4   190  12           184-215/0.07                           130  Cuttlefish oil                                                                           o  4   180  16           190-216/0.07                           131  Sardine oil                                                                              o  4   190  14           194-218/0.07                           132  Mackerel oil                                                                             o  4   190  15           193-200/0.06                           133  Saury pike oil                                                                           o  4   200  12           194-218/0.06                           134  Herring oil                                                                              o  4   200  12           196-218/0.04                           135  Saurel oil                                                                               o  4   200  12           189-214/0.06                           136  Flatfish oil                                                                             o  4   190  12           195-217/0.05                           137  Menhaden oil                                                                             o  4   190  14           193-214/0.04                           138  Liver oil o  4   190  12           193-226/0.06                           139  Residual oil                                                                             o  4   190  16           188-217/0.07                           __________________________________________________________________________                      Theo-                                                                               Ana- Theo-                                                                               Ana- Theo-                                                                               Ana-                                 Example                                                                             Ester or    reti-                                                                               lyti-                                                                               reti-                                                                               lyti-                                                                               reti-                                                                               lyti-                                No.  glyceride   cal  cal  cal  cal  cal  cal                                  __________________________________________________________________________     108  Methyl linoleate                                                                           81.40                                                                               81.58                                                                               10.77                                                                               10.93                                                                               3.65 3.44                                 109  Ethyl linoleate                                                                            81.40                                                                               81.56                                                                               10.77                                                                               10.80                                                                               3.65 3.38                                 110  Methyl oleate                                                                              80.98                                                                               81.21                                                                               11.24                                                                               1.42 3.63 3.44                                 111  Methyl isostearate                                                                         80.50                                                                               80.78                                                                               11.70                                                                               11.99                                                                               3.61 3.46                                 112  Methyl linolenate                                                                          81.83                                                                               81.89                                                                               10.30                                                                               10.56                                                                               3.67 3.39                                 __________________________________________________________________________      o R"" = CH.sub.3                                                               *R"" = C.sub.2 H.sub.5-                                                  

EXAMPLE 140

Linoleic acid chloride (30 g.) was dissolved in 50 ml. of anhydrous ether. The solution was added dropwise with cooling and stirring at 0°-5° C. to a mixture of 12.5 g. of l(-)α-methylbenzylamine, 100 ml. of anhydrous ether and 8 g. of trimethylamine. After completion of the dropwise addition, the reaction mixture was boiled for 2 hours to complete the reaction. The ether solution of the reaction product was washed with acid, alkali and water and was then dried, concentrated and distilled to obtain 42 g. of a desired product, b.p. 209°-218° C./0.05 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.46          81.38                                               H (%)       10.77          10.81                                               N (%)        3.45           3.61                                               ______________________________________                                    

Examples 141-175 are shown in the following table:

    __________________________________________________________________________                                           C %     H %      N %                                              Condensa-    Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana- Theo-                                                                              Ana-                Ex.                                                                               Acid halide           tion  b.p.   reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                               reti-                                                                              lyti-               No.                                                                                Acid      x   Solvent                                                                               assistant                                                                            ° C./mmHg                                                                      cal cal cal cal  cal cal                 __________________________________________________________________________     141                                                                               Oleic acid Cl                                                                               o Acetone                                                                               K.sub.2 CO.sub.3                                                                     208-217/0.05                                                                          80.98                                                                              81.14                                                                              11.24                                                                              11.40                                                                               3.63                                                                               3.94                142                                                                               Oleic acid Cl                                                                               o Tetrahydro-                                                                           NaOH  207-217/0.05                                                                          80.98                                                                              81.08                                                                              11.24                                                                              11.30                                                                               3.63                                                                               3.65                                  furan-water                                                  143                                                                               Isostearic acid                                                                           Cl                                                                               o Ether  Trimethyl-                                                                           206-219/0.06                                                                          80.56                                                                              80.74                                                                              11.70                                                                              11.92                                                                               3.61                                                                               3.40                                         amine                                                 144                                                                               Isostearic acid                                                                           Cl                                                                               o Toluene                                                                               Pyridine                                                                             203-217/0.05                                                                          80.56                                                                              80.71                                                                              11.70                                                                              11.85                                                                               3.61                                                                               3.40                145                                                                               Linoletic acid                                                                            Cl                                                                               o Acetone                                                                               Picoline                                                                             206-213/0.05                                                                          81.40                                                                              81.64                                                                              10.77                                                                              10.83                                                                               3.65                                                                               3.69                146                                                                               Linoleic acid                                                                             Cl                                                                               o Methylbutyl-                                                                          Triethyl-                                                                            203-216/0.06                                                                          81.40                                                                              81.73                                                                              10.77                                                                              10.92                                                                               3.65                                                                               3.37                                  ketone amine                                                 147                                                                               Linolenic acid                                                                            Cl                                                                               o Ether  Triethyl-                                                                            202-218/0.05                                                                          81.83                                                                              81.92                                                                              10.30                                                                              10.54                                                                               3.67                                                                               3.44                                         amine                                                 148                                                                               Linolenic acid                                                                            Cl                                                                               o Benzene                                                                               Dimethyl-                                                                            204-216/0.04                                                                          81.83                                                                              81.96                                                                              10.30                                                                              10.65                                                                               3.67                                                                               3.45                                         aniline                                               149                                                                               Safflower oil acid                                                                        Cl                                                                               * Dioxane-                                                                              KOH   197-208/0.05                                                      water                                                        150                                                                               Safflower oil acid                                                                        Cl                                                                               o Dioxane-                                                                              KOH   198-211/0.05                                                      water                                                        151                                                                               Soybean oil acid                                                                          Cl                                                                               o Acetone-                                                                              K.sub.2 CO.sub.3                                                                     196-210/0.06                                                      water                                                        152                                                                               Sesame oil acid                                                                           Cl                                                                               o Ether  Pyridine                                                                             198-214/0.06                                    153                                                                               Castor oil acid                                                                           Cl                                                                               o Ether  Pyridine                                                                             193-218/0.04                                    154                                                                               Rape-seed oil acid                                                                        Cl                                                                               o Ether  Pyridine                                                                             201-227/0.06                                    155                                                                               Olive oil acid                                                                            Cl                                                                               * Toluene                                                                               Trimethyl-                                                                           186-213/0.05                                                             amine                                                 156                                                                               Rica bran oil acid                                                                        Cl                                                                               o toluene                                                                               Triethyl-                                                                            186-215/0.06                                                             amine                                                 157                                                                               Cottonseed oil acid                                                                       Cl                                                                               o Benzene                                                                               Pyridine                                                                             194-213/0.05                                    158                                                                               Chrysalis oil acid                                                                        Cl                                                                               o Toluene                                                                               Pyridine                                                                             190-212/0.06                                    159                                                                               Corn oil acid                                                                             Cl                                                                               o Acetone-                                                                              NaOH  208-221/0.08                                                      water                                                        160                                                                               Linseed oil acid                                                                          Cl                                                                               o Ether  Pyridine                                                                             190-211/0.06                                    161                                                                               Sunflower oil acid                                                                        Cl                                                                               o Tetrahydro-                                                                           NaOH  195-212/0.05                                                      furan-water                                                  162                                                                               Flatfish oil acid                                                                         Cl                                                                               o Methylbutyl-                                                                          K.sub.2 CO.sub.3                                                                     189-215/0.04                                                      ketone                                                       163                                                                               Shark oil acid                                                                            Cl                                                                               * Acetone-                                                                              NaOH  185-218/0.04                                                      water                                                        164                                                                               Whale oil acid                                                                            Cl                                                                               o Acetone-                                                                              Na.sub.2 CO.sub.3                                                                    184-209/0.05                                                      water                                                        165                                                                               Cuttlefish oil acid                                                                       Cl                                                                               o Dioxane-                                                                              NaOH  186-217/0.05                                                      water                                                        166                                                                               Sardine oil acid                                                                          Cl                                                                               * Dioxane-                                                                              K.sub.2 CO.sub.3                                                                     198-218/0.05                                                      water                                                        167                                                                               Mackerel oil acid                                                                         Cl                                                                               o Toluene                                                                               Pyridine                                                                             195-211/0.05                                    168                                                                               Saury pike oil acid                                                                       Cl                                                                               o Dioxane-                                                                              NaOH  199-210/0.05                                                      water                                                        169                                                                               Herring oil acid                                                                          Cl                                                                               o Toluene                                                                               Pyridine                                                                             193-217/0.05                                    170                                                                               Saurel oil acid                                                                           Cl                                                                               o Acetone-                                                                              NaOH  183-214/0.05                                                      water                                                        171                                                                               Menhaden oil acid                                                                         Cl                                                                               o Toluene                                                                               Pyridine                                                                             195-225/0.05                                    172                                                                               Cod-oil acid                                                                              Cl                                                                               o Acetone-                                                                              KOH   184-208/0.05                                                      water                                                        173                                                                               Liver oil acid                                                                            Cl                                                                               * Ether  Pyridine                                                                             196-215/0.04                                    174                                                                               Residual oil acid                                                                         Cl                                                                               o Acetone-                                                                              KOH   188-218/0.06                                                      water                                                        175                                                                               Menuke oil acid                                                                           Cl                                                                               o Acetone-                                                                              NaOH  189-205/0.06                                                      water                                                        __________________________________________________________________________

EXAMPLE 176

A mixture of 100 g. of safflower oil, 43 g. of d(+)α-methyl-benzylamine and 2 g. of boric acid was heated at 140° C. for 7 hours. Subsequently, the reaction product was dissolved in ether. The resulting solution was washed with 5% hydrochloric acid water, 5% caustic soda water and water, and was dried, concentrated and distilled to obtain 121 g. of a desired product, b.p. 202°-209° C./0.04 mmHg.

Examples 177-223 are shown in the following tables:

    __________________________________________________________________________      ##STR193##                                                                                           Reaction                                                                             Reaction                                          Example                time  temperature     Boric                             No.   Glyceride                                                                              Amine R""                                                                               (hr)  ° C.                                                                           b.p. ° C./mmHg                                                                   acid                              __________________________________________________________________________     177   Linseed oil                                                                            d (+)                                                                               CH.sub.3                                                                           4      140°                                                                          201-222/0.05                                                                            5                                 178   Soybean oil                                                                            l (- )                                                                              CH.sub.3                                                                           4     "      200-218/0.06                                                                            5                                 179   Sunflower oil                                                                          d (+)                                                                               C.sub.2 H.sub.5                                                                    4     "      198-219/0.06                                                                            3                                 180   Rice bran oil                                                                          d (+)                                                                               C.sub.2 H.sub.5                                                                    6     "      201-223/0.04                                                                            1                                 181   Corn oil                                                                               d (+)                                                                               C.sub.3 H.sub.7                                                                    6     "      200-219/0.05                                                                            1                                 182   Sesame oil                                                                             l (-)                                                                               C.sub.3 H.sub.7                                                                    5     "      189-213/0.03                                                                            2                                 183   Cottonseed oil                                                                         l (-)                                                                               C.sub.4 H.sub.9                                                                    6     150    203-230/0.07                                                                            1                                 184   Castor oil                                                                             d (+)                                                                               C.sub.4 H.sub.9                                                                    6     140    205-218/0.06                                                                            1                                 185   Shark oil                                                                              l (-)                                                                               CH.sub.3                                                                           4     "      193-223/0.05                                                                            3                                 186   Cuttlefish oil                                                                         d (+)                                                                               CH.sub.3                                                                           6     "      190-222/0.05                                                                            1                                 187   Sardine oil                                                                            l (-)                                                                               C.sub.2 H.sub.5                                                                    6     "      198-224/0.05                                                                            1                                 188   Mackerel oil                                                                           l (-)                                                                               C.sub.2 H.sub.5                                                                    8     "      200-218/0.06                                                                              0.5                             189   Saury pike oil                                                                         d (+)                                                                               CH.sub.3                                                                           5     "      202-218/0.06                                                                            1                                 190   Herring oil                                                                            l (-)                                                                               CH.sub.3                                                                           8     "      188-219/0.05                                                                            1                                 191   Saurel oil                                                                             d (+)                                                                               CH.sub.3                                                                           5     160    199-228/0.04                                                                            2                                 192   Cod oil l (-)                                                                               C.sub.3 H.sub.7                                                                    4     160    206-232/0.02                                                                            2                                 193   Flatfish oil                                                                           d (+)                                                                               C.sub.4 H.sub.9                                                                    6     "      200-223/0.05                                                                            2                                 194   Whale oil                                                                              d (+)                                                                               CH.sub.3                                                                           7     "      200-218/0.05                                                                            1                                 __________________________________________________________________________

    __________________________________________________________________________     Acid or Ester                                                                  195  Linseed oil H      d (+) CH.sub.3                                                                             5   145°                                                                          201-222/0.05                                                                               3                    196  Soybean oil H      l (-) CH.sub.3                                                                             5   145°                                                                          200-219/0.05                                                                               3                    197  Sunflower oil                                                                              H      d (+) CH.sub.3                                                                             5   145°                                                                          196-221/0.05                                                                               3                    198  Rice bran oil                                                                              CH.sub.3                                                                              d (+) CH.sub.3                                                                             5   145°                                                                          203-225/0.05                                                                               3                    199  Corn oil    CH.sub.3                                                                              d (+) C.sub.2 H.sub.5                                                                      5   145°                                                                          200-220/0.06                                                                               3                    200  Sesame oil  H      l (-) CH.sub.3                                                                             5   145°                                                                          188-215/0.03                                                                               3                    201  Cottonseed oil                                                                             CH.sub.3                                                                               l (-)                                                                               C.sub.2 H.sub.5                                                                      5   145°                                                                          205-230/0.05                                                                               3                    202  Castor oil  CH.sub.3                                                                               l (-)                                                                               CH.sub.3                                                                             6   145°                                                                          208-219/0.04                                                                               3                    203  Shark oil   H      d (+) C.sub.2 H.sub.5                                                                      5   145°                                                                          198-225/0.05                                                                               3                    204  Cuttlefish oil                                                                             CH.sub.3                                                                              d (+) C.sub.3 H.sub.7                                                                      7   145°                                                                          188-224/0.05                                                                               2                    205  Sardine oil   C.sub.2 H.sub.5                                                                     d (+) C.sub.3 H.sub.7                                                                      7   145°                                                                          198-225/0.05                                                                               1                    206  Mackerel oil                                                                               H      d (+) CH.sub.3                                                                             5   145°                                                                          200-218/0.06                                                                               3                    207  Saury pike oil                                                                              C.sub.3 H.sub.7                                                                       l (-)                                                                               C.sub.4 H.sub.9                                                                      7   145°                                                                          200-220/0.07                                                                               3                    208  Herring oil H      d (+) C.sub.4 H.sub.9                                                                      8   145°                                                                          189-219/0.05                                                                               1                    209  Saurel oil  CH.sub.3                                                                               l (-)                                                                               CH.sub.3                                                                             8   145°                                                                          198-230/0.03                                                                               1                    210  Cod oil     H      l (-) C.sub.3 H.sub.7                                                                      8   145°                                                                          208-230/0.02                                                                               1                    211  Flatfish oil                                                                               H      l (-) C.sub.4 H.sub.9                                                                      5   145°                                                                          200-225/0.04                                                                               3                    212  Whale oil   H      d (+) CH.sub.3                                                                             7   145°                                                                          200-219/0.05                                                                               3                                       Reac-                                                                               Reac-         C %      H %      N %                                       tion                                                                               tion                             Theo-                                                                              Ana-               Example                                                                             RCOOA         time                                                                               temper-                                                                            Boric      Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             reti-                                                                              lyti-              No.  R   A   R""   (hr)                                                                               ature                                                                              acid                                                                              b.p. °C./mmHg                                                                   tical                                                                               tical                                                                              tical                                                                               tical                                                                              cal cal                __________________________________________________________________________     213  C.sub.17 H.sub.29                                                                  H   d (+) CH.sub.3                                                                       5   150 2  203-223/0.05                                                                           81.83                                                                               81.67                                                                              10.30                                                                               10.17                                                                              3.67                                                                               3.66               214  C.sub.17 H.sub.29                                                                  CH.sub.3                                                                            l (-) CH.sub.3                                                                      5   145 2  203-225/0.04                                                                           81.83                                                                               81.78                                                                              10.30                                                                               10.17                                                                              3.67                                                                               3.69               215  C.sub.17 H.sub.31                                                                  H   l (-) CH.sub.3                                                                       5   140 2  200-219/0.05                                                                           81.40                                                                               81.19                                                                              10.77                                                                               10.69                                                                              3.65                                                                               3.87               216  C.sub.17 H.sub.31                                                                  CH.sub.3                                                                           d (+) C.sub.2 H.sub.5                                                                8   145 1  204-221/0.05                                                                           81.55                                                                               81.49                                                                              10.90                                                                               10.81                                                                              3.52                                                                               3.42               217  C.sub.17 H.sub.31                                                                  C.sub.2 H.sub.5                                                                    d (+) C.sub.2 H.sub.5                                                                6   145 1  200-219/0.05                                                                           81.55                                                                               81.38                                                                              10.90                                                                               10.80                                                                              3.52                                                                               3.65               218  Iso-                                                                               H   d (+) CH.sub.3                                                                       4   145 3  200-200/0.06                                                                           80.56                                                                               80.33                                                                              11.70                                                                               11.54                                                                              3.61                                                                               3.65                    C.sub.17 H.sub.35                                                         219  Iso-                                                                               H   l (-) CH.sub.3                                                                       5   145 3  206-216/0.05                                                                           80.56                                                                               80.42                                                                              11.70                                                                               11.43                                                                              3.61                                                                               3.71                    C.sub.17 H.sub.35                                                         220  Iso-                                                                               H   l (-) C.sub.2 H.sub.5                                                                8   140 2  205-219/0.05                                                                           80.73                                                                               80.69                                                                              11.80                                                                               11.79                                                                              3.49                                                                               3.39                    C.sub.17 H.sub.35                                                         221  C.sub.17 H.sub.31                                                                  H   d (+) CH.sub.3                                                                       8   140 2  200-209/0.05                                                                           81.40                                                                               81.31                                                                              10.77                                                                               10.65                                                                              3.65                                                                               3.49               222  C.sub.17 H.sub.31                                                                  CH.sub.3                                                                           d (+) C.sub.3 H.sub.7                                                                5   145 4  200-208/0.05                                                                           81.69                                                                               81.49                                                                              11.02                                                                               11.00                                                                              3.40                                                                               3.51               223  C.sub.17 H.sub.33                                                                  H   l (-) CH.sub.3                                                                       4   145 3  201-205/0.01                                                                           80.98                                                                               80.88                                                                              11.24                                                                               11.21                                                                              3.63                                                                               3.62               __________________________________________________________________________

EXAMPLE 224

A mixture of 10 g. of linoleic acid and 5 g. of (+)α-methylbenzylamine was heated for about 8 hours in 300 ml. of toluene in the presence of 0.2 g. of p-toluenesulfonic acid, using a water separator.

After completion of the reaction, the toluene layer was washed with aqueous solution of acid, alkali and with water and dried and concentrated to obtain 12.1 g. of a desired product, b.p. 200°-211° C./0.05 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.40          81.71                                               H (%)       10.77          10.93                                               N (%)        3.65           3.38                                               ______________________________________                                    

Examples 225-259 are shown in the following table, in which:

Dehydration agent:

A. p-Toluenesulfonic acid

B. p-Toluenesulfonic acid chloride

C. sulfuric acid

D. phenolsulfonic acid

E. ira-400

f. amberlist-15

Solvent:

a. Toluene

b. Pyridine

c. Benzene

d. Chloroform

e. Xylene

f. Carbon tetrachloride

    __________________________________________________________________________      ##STR194##                                                                                    Dehyd-  Reac-                                                                  ration  tion        C %      H %      N %                      Example         assis-                                                                             Sol-                                                                               time                                                                               b.p.    Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-              No.  Fatty acid                                                                            R"" tant                                                                               vent                                                                               (hr)                                                                               ° C./mmHg                                                                       tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical               __________________________________________________________________________     225  Oleic acid                                                                            CH.sub.3                                                                           A   a    8  203-211/0.05                                                                           80.98                                                                               81.21                                                                              11.24                                                                               11.45                                                                              3.63 3.45                226  Oleic acid                                                                            CH.sub.3                                                                           B   b   20  205-216/0.07                                                                           80.98                                                                               81.19                                                                              11.24                                                                               11.41                                                                              3.63 3.49                227  Linoleic acid                                                                         CH.sub.3                                                                           A   d   10  200-211/0.05                                                                           81.40                                                                               81.63                                                                              10.77                                                                               10.93                                                                              3.65 3.41                228  Linoleic acid                                                                         CH.sub.3                                                                           D   e   10  201-210/0.05                                                                           81.40                                                                               81.66                                                                              10.77                                                                               10.97                                                                              3.65 3.43                229  Linolenic acid                                                                        CH.sub.3                                                                           A   a   10  201-213/0.05                                                                           81.83                                                                               82.09                                                                              10.30                                                                               10.61                                                                              3.67 6.32                230  Linolenic acid                                                                        CH.sub.3                                                                           E   e   10  200-212/0.05                                                                           81.83                                                                               82.12                                                                              10.30                                                                               10.59                                                                              3.67 6.41                231  Isostearic acid                                                                       CH.sub.3                                                                           A   f   12  206-218/0.04                                                                           80.56                                                                               80.78                                                                              11.70                                                                               11.76                                                                              3.61 3.58                232  Isostearic acid                                                                       CH.sub.3                                                                           B   b   20  201-219/0.06                                                                           80.56                                                                               80.79                                                                              11.70                                                                               11.98                                                                              3.61 3.40                233  Safflower oil                                                                         C.sub.2 H.sub.5                                                                    F   e    8  205-217/0.06                                       234  Soybean oil                                                                           CH.sub.3                                                                           A   e    8  201-210/0.05                                       235  Sesame oil                                                                            CH.sub.3                                                                           A   e    8  200-213/0.06                                       236  Castor oil                                                                            CH.sub.3                                                                           A   d    8  197-215/0.05                                       237  Corn oil                                                                              C.sub.2 H.sub.5                                                                    B   b   20  186-218/0.05                                       238  Cottonseed oil                                                                        CH.sub.3                                                                           A   f    8  189-209/0.06                                       239  Olive oil                                                                             CH.sub.3                                                                           D   a    8  183-208/0.05                                       240  Linseed oil                                                                           CH.sub.3                                                                           C   a   10  187-211/0.05                                       241  Rape-seed oil                                                                         CH.sub.3                                                                           A   a   12  193-216/0.06                                       242  Rice bran oil                                                                         CH.sub.3                                                                           A   a    8  193-210/0.05                                       243  Chrysalia oil                                                                         CH.sub.3                                                                           C   a    8  188-214/0.06                                       244  Sunflower oil                                                                         CH.sub.3                                                                           A   e    8  191-213/0.06                                       245  Flatfish oil                                                                          CH.sub.3                                                                           D   e    8  190-220/0.05                                       246  Shark oil                                                                             CH.sub.3                                                                           A   a   10  187-209/0.06                                       247  Whale oil                                                                             CH.sub.3                                                                           E   a   10  187-220/0.05                                       248  Cuttlefish oil                                                                        CH.sub.3                                                                           A   a    8  193- 218/0.06                                      249  Sardine oil                                                                           CH.sub.3                                                                           B   b   20  201-219/0.06                                       250  Mackerel oil                                                                          CH.sub.3                                                                           F   a    8  200-218/0.05                                       251  Saury pike oil                                                                        C.sub.2 H.sub.5                                                                    A   c    8  187-217/0.06                                       252  Herring oil                                                                           CH.sub.3                                                                           C   d   10  185-215/0.05                                       253  Saurel oil                                                                            CH.sub.3                                                                           A   a   10  184-212/0.05                                       254  Manhaden oil                                                                          CH.sub.3                                                                           A   a   10  182-222/0.08                                       255  Cod oil                                                                               CH.sub.3                                                                           A   e    8  190-218/0.05                                       256  Liver oil                                                                             CH.sub.3                                                                           D   f   12  189-217/0.06                                       257  Residual oil                                                                          CH.sub.3                                                                           A   a    8  184-221/0.08                                       258  Menuke oil                                                                            CH.sub.3                                                                           A   e    8  175-220/0.08                                       259  Safflower oil                                                                         C.sub.3 H.sub.7                                                                    A   e   12  199-211/0.04                                       __________________________________________________________________________

EXAMPLE 260

A mixture of 10 g. of methyl linoleate and 6 g. of (+)α-methylbenzylamine was heated at 180° C. for 30 hours in a nitrogen atmosphere, while excluding by-produced methanol out of the reaction system. After completion of the reaction, the reaction mixture was distilled to obtain 12.3 g. of a desired product, b.p. 202°-215° C./0.05 mmHg, [α]D₂₅ + 59.5. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.40          81.62                                               H (%)       10.77          10.85                                               N (%)        3.65           3.46                                               ______________________________________                                    

EXAMPLE 261

A mixture of 10 g. of methyl isostearate was mixed with 5 g. of (+)α-methylbenzylamine and 1 g. of sodium methylate. The mixture was reacted at 150° C. for 3 hours while excluding by-produced methanol out of the reaction system. The reaction mixture was washed with acid, alkali and water according to ordinary procedures and was dried and distilled to obtain 12.3 g. of a desired product, b.p. 207°-220° C./0.06 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.56          80.49                                               H (%)       11.70          11.77                                               N (%)        3.61           3.81                                               ______________________________________                                    

EXAMPLE 262

To a mixture of 10 g. of ethyl oleate and 5 g. of (+)α-methylbenzylamine was added a solution of 0.5 g. of sodium in 8 ml. of ethyl alcohol. The mixture was reacted at 160° C. for about 2 hours removing ethyl alcohol. Thereafter, the same treatments as in Example 261 were effected to obtain 12.0 g. of a desired product, b.p. 208°-219° C./0.06 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.98          80.88                                               H (%)       11.24          11.17                                               N (%)        3.63           3.81                                               ______________________________________                                    

EXAMPLE 263

A mixture of 10 g. of safflower oil and 6 g. of (+)α-methylbenzylamine was heated in an autoclave at 200° C. for 12 hours and was then immediately distilled to obtain 13.0 g. of a desired product, b.p. 197°-220° C./0.05 mmHg.

Examples 264-296 are shown in the following table:

    __________________________________________________________________________      ##STR195##                                                                                          Refer-                                                                             Reac-                                                                               Reac-                                                                 ence                                                                               tion tion                                            Example               ex- temper-                                                                             time Cata-                                                                               Sol-                                                                               b.p.                              No.  Ester or glyceride                                                                          R"" ample                                                                              ature                                                                               (hr) lyst vent                                                                               ° C./mmHg                  __________________________________________________________________________     264  Methyl linoleate                                                                            o   263 200  12            200-211/0.04                      265  Ethyl linoleate                                                                             o   260 180  48            201-209/0.05                      266  Methyl oleate                                                                               o   261 160  4    KOtBu    204-221/0.06                      267  Methyl isostearate                                                                          o   262 160  2    NaOCH.sub.3,CH.sub.3 OH                                                                 206-219/0.07                      268  Methyl linolenate                                                                           o   263 200  14            205-218/0.05                      Safflower oil                                                                       0            263 200 14        198-209/0.05                                    methyl ester                                                              270  Sesame oil methyl                                                                           o   263 200  12            198-211/0.05                           ester                                                                     271  Castor oil methyl                                                                           o   260 180  42            199-215/0.05                           ester                                                                     272  Rape-seed oil                                                                               *   260 180  40            201-220/0.06                           methyl ester                                                              273  Olive oil methyl                                                                            o   261 150  3    NaOCH.sub.3                                                                             188-209/0.55                           ester                                                                     274  Rice bran oil                                                                               o   263 190  10            189-211/0.05                           methyl ester                                                              275  Cottonseed oil                                                                              *   260 180  38            193-208/0.05                           methyl ester                                                              276  Chrysalis oil                                                                               o   260 180  38            193-212/0.06                           methyl ester                                                              277  Sardine oil methyl                                                                          o   260 180  42            187-215/0.05                           ester                                                                     278  Fish oil methyl ester                                                                       o   260 180  42            187-208/0.05                      279  Flatfish oil methyl                                                                         o   260 180  36            197-223/0.05                           ester                                                                     280  Safflower oil                                                                               *   263 190  20            199-210/0.05                      281  Linseed oil  o   263 190  18            187-216/0.06                      282  Soybean oil  o   263 190  18            196-217/0.06                      283  Sunflower oil                                                                               o   263 200  12            194-212/0.06                      284  Corn oil     o   263 200  12            195-213/0.07                      285  Shark oil    o   263 190  12            184-216/0.07                      286  Cuttlefish oil                                                                              o   263 180  16            189-217/0.07                      287  Sardine oil  o   263 190  14            191-213/0.07                      288  Mackerel oil o   263 190  15            193-209/0.06                      289  Saury pike oil                                                                              o   263 200  12            194-213/0.06                      290  Herring oil  o   263 200  12            196-213/0.04                      291  Saurel oil   o   263 200  12            188-214/0.06                      292  Flatfish oil o   263 190  12            196-217/0.05                      293  Menhaden oil o   263 190  14            193-219/0.04                      294  Liver oil    o   263 190  12            193-220/0.06                      295  Residual oil o   263 190  16            188-218/0.07                      296  Safflower oil    263 200  18            200-209/0.02                            (R""=C.sub.3 H.sub.7)                                                    __________________________________________________________________________                       C%          H %         N %                                                    Theo- Ana-  Theo- Ana-  Theo- Ana-                           Example           reti- lyti- reti- lyti- reti- lyti-                          No.  Ester or glyceride                                                                          cal   cal   cal   cal   cal   cal                            __________________________________________________________________________     264  Methyl linoleate                                                                            81.40 81.59 10.77 10.91 3.65  3.44                           265  Ethyl linoleate                                                                             81.40 81.58 10.77 10.88 3.65  3.33                           266  Methyl oleate                                                                               80.98 81.20 11.24 11.44 3.63  3.42                           267  Methyl isostearate                                                                          80.56 80.77 11.70 11.98 3.61  3.47                           268  Methyl linolenate                                                                           81.83 81.88 10.30 10.55 3.67  3.29                           269  Safflower oil                                                                  methyl ester                                                              270  Sesame oil methyl                                                              ester                                                                     271  Castor oil methyl                                                              ester                                                                     272  Rape-seed oil                                                                  methyl ester                                                              273  Olive oil methyl                                                               ester                                                                     274  Rice bran oil                                                                  methyl ester                                                              275  Cottonseed oil                                                                 methyl ester                                                              276  Chrysalis oil                                                                  methyl ester                                                              277  Sardine oil methyl                                                             ester                                                                     278  Fish oil methyl ester                                                     279  Flatfish oil methyl                                                            ester                                                                     280  Safflower oil                                                             281  Linseed oil                                                               282  Soybean oil                                                               283  Sunflower oil                                                             284  Corn oil                                                                  285  Shark oil                                                                 286  Cuttlefish oil                                                            287  Sardine oil                                                               288  Mackerel oil                                                              289  Saury pike oil                                                            290  Herring oil                                                               291  Saurel oil                                                                292  Flatfish oil                                                              293  Menhaden oil                                                              294  Liver oil                                                                 295  Residual oil                                                              296  Safflower oil                                                                   (R""=C.sub.3 H.sub.7)                                                    __________________________________________________________________________      o R"" = CH.sub.3                                                               * R"" C.sub.2 H.sub.5?                                                   

EXAMPLE 297

Linoleic acid (10 g.), 5 g. of d(+)α-methylbenzylamine and 10 g. of dicyclohexyl carbodiimide were individually dissolved in 50 ml. of toluene. The solutions were mixed together at one time, and the mixed solution was allowed to stand at room temperature for 8 hours. After filtering the solution, the filtrate was washed with acid alkali and water and was dried concentrated and distilled to obtain 11.1 g. of a desired product, b.p. 201°-209° C./0.04 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.40          81.66                                               H (%)       10.77          10.91                                               N (%)        3.65           3.42                                               ______________________________________                                    

Examples 298-332 are shown in the following table:

    __________________________________________________________________________      ##STR196##                                                                                                        C %      H %      N %                      Ex.         Amine                                                                              BNCNB         b.p.  Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-              No.                                                                               Acid     R"" B      Solvent                                                                               ° C./mmHg                                                                     tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical               __________________________________________________________________________     298                                                                               Linoleic acid                                                                           CH.sub.3                                                                            ##STR197##                                                                           Ether  200-209/ 0.04                                                                        81.40                                                                               81.67                                                                              10.77                                                                               10.93                                                                              3.65 3.44                299                                                                               Linoleic acid                                                                           CH.sub.3                                                                            ##STR198##                                                                           Dioxane                                                                               201-209/ 0.04                                                                        81.40                                                                               81.68                                                                              10.77                                                                               10.91                                                                              3.65 3.33                300                                                                               Oleic acid                                                                              CH.sub.3                                                                            ##STR199##                                                                           Dioxane                                                                               203-109/ 0.06                                                                        80.98                                                                               81.05                                                                              11.24                                                                               11.44                                                                              3.63 3.48                301                                                                               Linolenic acid                                                                          CH.sub.3                                                                            ##STR200##                                                                           Tetrahydro- furan                                                                     205-211/ 0.05                                                                        81.83                                                                               82.05                                                                              10.30                                                                               10.65                                                                              3.67 3.49                302                                                                               Isostearic acid                                                                         CH.sub.3                                                                            ##STR201##                                                                           Ether  203-214/ 0.07                                                                        80.56                                                                               80.72                                                                              11.70                                                                               11.97                                                                              3.61 3.51                303                                                                               Isostearic acid                                                                         CH.sub.3                                                                            ##STR202##                                                                           Toluene                                                                               200- 214/ 0.05                                                                       80.56                                                                               80.88                                                                              11.70                                                                               11.87                                                                              3.61 3.49                304                                                                               Safflower oil                                                                           C.sub.2 H.sub.5                                                                     ##STR203##                                                                           Toluene                                                                               199-214/ 0.05                                    305                                                                               Soybean oil                                                                             CH.sub.3                                                                            ##STR204##                                                                           Chloroform                                                                            195-213/ 0.05                                    306                                                                               Sesame oil                                                                              CH.sub.3                                                                            ##STR205##                                                                           Toluene                                                                               189-216/ 0.07                                    307                                                                               Castor oil                                                                              CH.sub.3                                                                            ##STR206##                                                                           Tetra- chloro- carbon                                                                 192-213/ 0.07                                    308                                                                               Rape-seed oil                                                                           CH.sub.3                                                                            ##STR207##                                                                           Benzene                                                                               191-211/ 0.06                                    309                                                                               Olive oil                                                                               C.sub.2 H.sub.5                                                                     ##STR208##                                                                           Pyridine                                                                              190-215/ 0.06                                    310                                                                               Rice bran oil                                                                           CH.sub.3                                                                            ##STR209##                                                                           Benzene                                                                               185-214/ 0.06                                    311                                                                               Cottonseed oil                                                                          CH.sub.3                                                                            ##STR210##                                                                           Toluene                                                                               193-215/ 0.05                                    312                                                                               Corn oil CH.sub.3                                                                            ##STR211##                                                                           Toluene                                                                               190-213/ 0.05                                    313                                                                               Peanut oil                                                                              CH.sub.3                                                                            ##STR212##                                                                           Ether  192-218/ 0.06                                    314                                                                               Olive oil                                                                               CH.sub.3                                                                            ##STR213##                                                                           Toluene                                                                               191-219/ 0.06                                    315                                                                               Chrysalis oil                                                                           CH.sub.3                                                                            ##STR214##                                                                           Toluene                                                                               190-215/ 0.05                                    316                                                                               Shark oil                                                                               CH.sub.3                                                                            ##STR215##                                                                           Benzene                                                                               204-222/ 0.05                                    317                                                                               Cuttlefish oil                                                                          CH.sub.3                                                                            ##STR216##                                                                           Toluene                                                                               179-223/ 0.05                                    318                                                                               Sardine oil                                                                             CH.sub.3                                                                            ##STR217##                                                                           Ether  190-220/ 0.07                                    319                                                                               Mackerel oil                                                                            CH.sub.3                                                                            ##STR218##                                                                           Ether  192-215/ 0.05                                    320                                                                               Saury pike oil                                                                          CH.sub.3                                                                            ##STR219##                                                                           Benzene                                                                               190-211/ 0.06                                    321                                                                               Herring oil                                                                             CH.sub.3                                                                            ##STR220##                                                                           Ether  191-218/ 0.05                                    322                                                                               Saurel oil                                                                              CH.sub.3                                                                            ##STR221##                                                                           Toluene                                                                               181-219/ 0.05                                    323                                                                               Cod oil  CH.sub.3                                                                            ##STR222##                                                                           Chloroform                                                                            185-210/ 0.05                                    324                                                                               Trout oil                                                                               CH.sub.3                                                                            ##STR223##                                                                           Tetrahydro- furan                                                                     180-219/ 0.05                                    325                                                                               Gray mullet oil                                                                         CH.sub.3                                                                            ##STR224##                                                                           Tetrahydro- furan                                                                     191-225/ 0.05                                    326                                                                               Munuke oil                                                                              CH.sub.3                                                                            ##STR225##                                                                           Toluene                                                                               187-215/ 0.06                                    327                                                                               Menhaden oil                                                                            C.sub.2 H.sub.5                                                                     ##STR226##                                                                           Dioxane                                                                               193-225/ 0.05                                    328                                                                               Eel oil  CH.sub.3                                                                            ##STR227##                                                                           Benzene                                                                               196-220/ 0.05                                    329                                                                               Flatfish oil                                                                            CH.sub.3                                                                            ##STR228##                                                                           Dioxane                                                                               187-220/ 0.05                                    330                                                                               Whale oil                                                                               CH.sub.3                                                                            ##STR229##                                                                           Benzene                                                                               175-219/ 0.06                                    331                                                                               Liver oil                                                                               CH.sub.3                                                                            ##STR230##                                                                           Toluene                                                                               190-219/ 0.07                                    332                                                                               Residual oil                                                                            C.sub.2 H.sub.5                                                                     ##STR231##                                                                           Toluene                                                                               191-223/ 0.08                                    __________________________________________________________________________

EXAMPLE 333

To a solution of 12.5 g. of (+)α-methylbenzylamine and 8 g. of trimethylamine in 100 ml. of anhydrous ether was added 30 g. of linoleic acid chloride in 50 ml. of anhydrous ether under stirring at 0°-5° C. After addition, the reaction mixture was boiled for 2 hours to complete the reaction. Subsequently, the ether solution was washed with acid, alkali and water and dried, concentrated and distilled to obtain 42 g. of a desired product, b.p. 207°-217° C./0.05 mmHg. Elementary analysis:

              Theoretical  Analytical                                              ______________________________________                                         C (%)       81.46          81.58                                               H (%)       10.77          10.91                                               N (%)        3.65           3.41                                               ______________________________________                                    

Examples 334-369 are shown in the following table:

    __________________________________________________________________________     o α-Methyl-                                                                        * α-Ethylbenzylamine                                           Butylbenzylaminee       + α     α                                  benzylamine                                                                                                         C %     H %     N %                                               Conden-      Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                  Ex.                                                                               Acid halide          sation                                                                               b.p.   reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                 No.                                                                                acid  RCOX                                                                               X Solvent agent ° C./mmHg                                                                      cal cal cal cal cal cal                   __________________________________________________________________________     334                                                                               Oleic acid                                                                            o   Cl                                                                               Acetone K.sub.2 CO.sub.3                                                                     205-217/0.05                                                                          80.98                                                                              81.11                                                                              11.24                                                                              11.41                                                                              3.63                                                                               3.91                  335                                                                               Oleic acid                                                                            o   Cl                                                                               Tetrahydro-                                                                            NaOH  207-216/0.05                                                                          80.98                                                                              81.09                                                                              11.24                                                                              11.35                                                                              3.63                                                                               3.66                                  furan-water                                                    336                                                                               Isostearic acid                                                                       o   Cl                                                                               Ether   Trimethyl-                                                                           206-218/0.06                                                                          80.56                                                                              80.77                                                                              11.70                                                                              11.91                                                                              3.61                                                                               3.42                                          amine                                                  337                                                                               Isostearic acid                                                                       o   Cl                                                                               Toluene Pyridine                                                                             203-214/0.05                                                                          80.56                                                                              80.72                                                                              11.70                                                                              11.89                                                                              3.61                                                                               3.48                  338                                                                               Linoleic acid                                                                         o   Cl                                                                               Acetone Picoline                                                                             200-213/0.05                                                                          81.40                                                                              81.62                                                                              10.77                                                                              10.81                                                                              3.65                                                                               3.62                  339                                                                               Linoleic acid                                                                         o   Cl                                                                               Methylbutyl-                                                                           Triethyl-                                                                            200-216/0.06                                                                          81.40                                                                              81.70                                                                              10.77                                                                              10.94                                                                              3.65                                                                               3.33                                  ketone  amine                                                  340                                                                               Linolenic acid                                                                        o   Cl                                                                               Ether   Triethyl-                                                                            201-217/0.05                                                                          81.83                                                                              81.93                                                                              10.30                                                                              10.54                                                                              3.67                                                                               3.44                                          amine                                                  341                                                                               Linolenic acid                                                                        o   Cl                                                                               Benzene Dimethyl-                                                                            205-215/0.04                                                                          81.83                                                                              81.95                                                                              10.30                                                                              10.63                                                                              3.67                                                                               3.46                                          aniline                                                342                                                                               Safflower oil                                                                         *   Cl                                                                               Dioxane-water                                                                          KOH   198-208/0.05                                        acid                                                                        343                                                                               Soybean oil                                                                           o   Cl                                                                               Acetone-water                                                                          K.sub.2 CO.sub.3                                                                     195-210/0.06                                        acid                                                                        344                                                                               Sesame oil                                                                            o   Cl                                                                               Ether   Pyridine                                                                             198-211/0.06                                        acid                                                                        345                                                                               Castor oil                                                                            o   Cl                                                                               Ether   Pyridine                                                                             193-216/0.04                                     346                                                                               Rape-seed oil                                                                         o   Cl                                                                               Ether   Pyridine                                                                             201-222/0.06                                     347                                                                               Olive oil                                                                             *   Cl                                                                               Toluene Trimethyl-                                                                           188-213/0.05                                                             amine                                                  348                                                                               Rice bran oil                                                                         o   Cl                                                                               Toluene Triethyl-                                                                            187-213/0.06                                                             amine                                                  349                                                                               Cottonseed oil                                                                        o   Cl                                                                               Benzene Pyridine                                                                             194-218/0.05                                     350                                                                               Chrysalis acid                                                                        o   Cl                                                                               Toluene Pyridine                                                                             190-214/0.06                                     351                                                                               Corn oil                                                                              o   Cl                                                                               Acetone-water                                                                          NaOH  203-221/0.08                                     352                                                                               Linseed oil                                                                           o   Cl                                                                               Ether   Pyridine                                                                             190-215/0.06                                     353                                                                               Sunflower oil                                                                         o   Cl                                                                               Tetrahydro-                                                                            NaOH  193-212/0.05                                                     furan-water                                                    354                                                                               Flatfish oil                                                                          o   Cl                                                                               Methylbutyl-                                                                           K.sub.2 CO.sub.3                                                                     188-214/0.04                                                     ketone                                                         355                                                                               Shark oil                                                                             *   Cl                                                                               Acetone-water 183-218/0.04                                     356                                                                               Whale oil                                                                             o   Cl                                                                               Acetone-water                                                                          Na.sub.2 CO.sub.3                                                                    183-208/0.05                                     357                                                                               Cuttlefish oil                                                                        o   Cl                                                                               Dioxane-water                                                                          NaOH  180-214/0.05                                     358                                                                               Sardine oil                                                                           *   Cl                                                                               Dioxane-water                                                                          K.sub.2 CO.sub.3                                                                     190-213/0.05                                     359                                                                               Mackerel oil                                                                          o   Cl                                                                               Toluene Pyridine                                                                             192-211/0.05                                     360                                                                               Saury pike oil                                                                        o   Cl                                                                               Dioxane-water                                                                          NaOH  190-210/0.05                                     361                                                                               Herring oil                                                                           o   Cl                                                                               Toluene Pyridine                                                                             193-214/0.05                                     362                                                                               Saurel oil                                                                            o   Cl                                                                               Acetone-                                                                               NaOH  183-219/0.05                                                     water                                                          363                                                                               Menhaden oil                                                                          o   Cl                                                                               Toluene Pyridine                                                                             193-223/0.05                                     364                                                                               Cod oil                                                                               o   Cl                                                                               Acetone-                                                                               KOH   186-209/0.05                                                     water                                                          365                                                                               Liver oil                                                                             *   Cl                                                                               Ether   Pyridine                                                                             190-214/0.04                                     366                                                                               Residual oil                                                                          o   Cl                                                                               Acetone-water                                                                          KOH   187-219/0.06                                     367                                                                               Menuke oil                                                                            o   Cl                                                                               Acetone-water                                                                          NaOH  188-208/0.06                                     368                                                                               Safflower oil                                                                             Cl                                                                               Acetone-water                                                                          NaOH  193-206/0.06                                     369                                                                               Safflower oil                                                                         +   Cl                                                                               Acetone-water                                                                          NaOH  197-211/0.08                                     __________________________________________________________________________

EXAMPLE 370

A mixture of 10 g. of linoleic acid and 6 g. of d(+)α-methylbenzylamine was heated at 180° C. for 24 hours while removing water out of the reaction system during the reaction. After completion of the reaction, the reaction mixture was immediately distilled to obtain 11.3 g. of a desired product, b.p. 203° - 221° C./0.07 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.40          81.66                                               H(%)        10.77          10.90                                               N (%)        3.65           3.42                                               ______________________________________                                    

Examples 371-396 are as shown in the following table:

    __________________________________________________________________________      ##STR232##                                                                                       Reaction                                                                            Reaction     C %     H %      N %                      Example            temper-                                                                             time b.p.   Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-              No.  Acid       R""                                                                               ature                                                                               (hr.)                                                                               ° C./mmHg                                                                      tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical               __________________________________________________________________________     371  Isostearic acid                                                                           o  180  24   205-218/0.06                                                                          80.56                                                                               80.77                                                                              11.70                                                                               11.97                                                                              3.61 3.30                372  Oleic acid o  180  24   205-217/0.05                                                                          80.98                                                                               81.30                                                                              11.24                                                                               11.63                                                                              3.63 3.29                373  Linolenic acid                                                                            o  180  24   208-216/0.06                                                                          81.83                                                                               81.96                                                                              10.30                                                                               10.61                                                                              3.67 3.38                374  Safflower oil acid                                                                        o  180  24   195-219/0.07                                      375  Soybean oil acid                                                                          o  200  20   198-221/0.05                                      376  Corn oil acid                                                                             o  180  20   194-209/0.06                                      377  Cottonseed oil acid                                                                       x  180  24   196-213/0.05                                      378  Sesame oil acid                                                                           o  160  36   198-206/0.04                                      379  Castor oil acid                                                                           o  160  36   200-221/0.04                                      380  Olive oil acid                                                                            o  180  24   188-211/0.06                                      381  Rape-seed oil acid                                                                        o  180  24   200-216/0.05                                      382  Sunflower oil acid                                                                        o  180  24   193-211/0.06                                      383  Linseed-oil acid                                                                          o  180  24   188-216/0.05                                      384  Rice bran oil acid                                                                        o  180  24   189-215/0.07                                      385  Shark oil acid                                                                            x  180  24   184-220/0.05                                      386  Whale oil acid                                                                            o  180  26   172-223/0.04                                      387  Mackerel oil acid                                                                         o  180  24   193-209/0.06                                      388  Saurel oil acid                                                                           o  180  24   189-216/0.07                                      389  Cuttlefish oil acid                                                                       o   200*                                                                               18   186-217/0.06                                      390  Cod oil acid                                                                              o   200*                                                                               18   188-223/0.08                                      391  Herring oil acid                                                                          o   210*                                                                               18   193-212/0.04                                      392  Sardine oil acid                                                                          o  180  20   190-220/0.08                                      393  Flatfish oil acid                                                                         o  180  24   197-221/0.05                                      394  Manhaden oil acid                                                                         o  180  24   190-218/0.06                                      395  Liver oil acid                                                                            o  180  20   193-220/0.05                                      396  Residual oil acid                                                                         o  180  20   185-216/0.05                                      __________________________________________________________________________      *In an autoclave                                                               o R"" = CH.sub.3                                                               x R"" = C.sub.2 H.sub.5                                                  

EXAMPLE 397

To a solution of 14 g. of linoleic acid and 5.5 g. of triethylamine in 100 cc. of tetrahydrofuran was added 5.9 g. of ethyl chloroformate under stirring at -10° to -5° C. After addition, the stirring was continued at -5° C. for additional 20 minutes. Subsequently, 6.5 g. of d(+)α-methylbenzylamine was added dropwise with stirring at -5° C. After the dropwise addition, the ice water bath was removed and stirring was continued until the temperature reached room temperature. Subsequently, the temperature was gradually increased, and stirring was continued at 40° C. for 20 minutes. After cooling, tetrahydrofuran was removed by distillation under reduced pressure, and the residue was dissolved in ether. The solution was washed with cold dilute aqueous solution of hydrochloric acid, sodium carbonate and water, and was dried over anhydrous sodium carbonate. The ether was removed by distillation and the residue was distilled in vacuo to obtain 15.8 g. of a desired product, b.p. 202°-207° C./0.03 mmHg, [α]_(D) + 50.0. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.40          81.72                                               H (%)       10.77          10.89                                               N (%)        3.65           3.42                                               ______________________________________                                    

In the same manner as in Example 397, each 1 mole of fatty acids and each 1-1.1 moles of basic substances were individually dissolved in a solvent in an amount of 7 to 10 times the amount of the acid. To the solutions was added 1-1.1 moles of chloroformate dropwise under stirring at -5° to -10° C. After addition, the mixtures were stirred at said temperature for 10-30 minutes. Subsequently, each 1-1.1 moles of amine derivative was added dropwise under stirring to the solution. During about 10 minutes after addition, the reaction was completed essentially. In some case, if necessary, the mixtures were heated to 40°-50° C. Thereafter, the mixtures were treated according to ordinary procedures to obtain in 40-85% yields such compounds as seen in Examples 398 to 551, which are shown in the following tables:

    __________________________________________________________________________      ##STR233##                                                                                            C %      H %      N %                                  Example          b.p.   Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                          No.  Acid    R"" °C./mmHg                                                                       tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical                           __________________________________________________________________________     398  Linoleic acid                                                                          d-CH.sub.3                                                                         201-209/0.04                                                                          81.40                                                                               81.66                                                                              10.77                                                                               10.95                                                                              3.65 3.58                            399  Linoleic acid                                                                          l-CH.sub.3                                                                         200-209/0.04                                                                          81.40                                                                               81.58                                                                              10.77                                                                               10.84                                                                              3.65 3.63                            400  Oleic acid                                                                             d-CH.sub.3                                                                         205-209/0.04                                                                          80.98                                                                               81.04                                                                              11.24                                                                               11.34                                                                              3.63 3.58                            401  Linolenic acid                                                                         d-CH.sub.3                                                                         205-213/0.05                                                                          81.83                                                                               82.03                                                                              10.30                                                                               10.35                                                                              3.67 3.47                            402  Isostearic acid                                                                        d-CH.sub.3                                                                         202-214/0.07                                                                          80.56                                                                               80.62                                                                              11.70                                                                               11.97                                                                              3.61 3.52                            403  Isostearic acid                                                                        l-CH.sub.3                                                                         201-213/0.05                                                                          80.56                                                                               80.73                                                                              11.70                                                                               11.89                                                                              3.61 3.48                            404  Safflower oil                                                                          d-C.sub.2 H.sub.5                                                                  199-213/0.03                                                  405  Soybean oil                                                                            l-CH.sub.3                                                                         193-215/0.04                                                  406  Sesame oil                                                                             d-CH.sub.3                                                                         188-214/0.07                                                  407  Castor oil                                                                             d-CH.sub.3                                                                         194-211/0.07                                                  408  Rape-seed oil                                                                          l-CH.sub.3                                                                         190-210/0.06                                                  409  Olive oil                                                                              d-C.sub.2 H.sub.5                                                                  193-215/0.06                                                  410  Rice bran oil                                                                          l-CH.sub.3                                                                         185-210/0.06                                                  411  Cottonseed oil                                                                         d-CH.sub.3                                                                         195-214/0.05                                                  412  Corn oil                                                                               d-CH.sub.3                                                                         191-218/0.05                                                  413  Peanut oil                                                                             d-CH.sub.3                                                                         193-217/0.06                                                  414  Olive oil                                                                              d-CH.sub.3                                                                         191- 209/0.06                                                 415  Chrysalis oil                                                                          d-CH.sub.3                                                                         198-215/0.04                                                  416  Shark oil                                                                              d-CH.sub.3                                                                         202-222/0.04                                                  417  Cuttlefish oil                                                                         d-CH.sub.3                                                                         178-225/0.04                                                  418  Sardine oil                                                                            d-CH.sub.3                                                                         194-222/0.06                                                  419  Mackerel oil                                                                           l-CH.sub.3                                                                         191-214/0.05                                                  420  Saury pike oil                                                                         l-CH.sub.3                                                                         197-211/0.05                                                  421  Herring oil                                                                            d-CH.sub.3                                                                         191-218/0.05                                                  422  Saurel oil                                                                             d-CH.sub.3                                                                         184-219/0.05                                                  423  Cod oil l-CH.sub.3                                                                         185-214/0.05                                                  424  Trout oil                                                                              l-CH.sub.3                                                                         180-218/0.05                                                  425  Gray mullet oil                                                                        d-CH.sub.3                                                                         193-225/0.04                                                  426  Menuke oil                                                                             d-CH.sub.3                                                                         189-215/0.05                                                  427  Menhaden oil                                                                           l-C.sub.2 H.sub.5                                                                  193-225/0.05                                                  428  Eel oil d-CH.sub.3                                                                         195-219/0.05                                                  429  Flatfish oil                                                                           l-CH.sub.3                                                                         188-220/0.05                                                  430  Whale oil                                                                              l-CH.sub.3                                                                         178-219/0.06                                                  431  Liver oil                                                                              d-CH.sub.3                                                                         192-217/0.05                                                  432  Residual oil                                                                           d-C.sub.2 H.sub.5                                                                  191-222/0.08                                                  __________________________________________________________________________

    __________________________________________________________________________                                      C %       H %       N %                       Ex.                        b.p.  Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-               No.  Acid      Amine      °C./mmHg                                                                       tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                __________________________________________________________________________     433                                                                               Linoleic acid                                                                            ##STR234##   202-212/0.04                                                                          81.55                                                                               81.70                                                                               10.90                                                                               11.07                                                                               3.52 3.56                 434                                                                               Linoleic acid                                                                            ##STR235##   203-216/0.05                                                                          81.55                                                                               81.65                                                                               10.90                                                                               11.05                                                                               3.52 3.64                 435                                                                               Linoleic acid                                                                            ##STR236##   208-214/0.04                                                                          81.55                                                                               81.74                                                                               10.90                                                                               11.08                                                                               3.52 3.72                 436                                                                               Linoleic acid                                                                            ##STR237##   199-216/0.05                                                                          81.69                                                                               81.87                                                                               11.02                                                                               11.48                                                                               3.40 3.40                 437                                                                               Linoleic acid                                                                            ##STR238##   220-223/0.08                                                                          74.69                                                                               74.77                                                                               9.65 9.71 3.35 3.48                 438                                                                               Linoleic acid                                                                            ##STR239##   222-224/0.07                                                                          74.69                                                                               74.82                                                                               9.65 9.73 3.35 3.37                 439                                                                               Linoleic acid                                                                            ##STR240##   220-226/0.08                                                                          74.69                                                                               74.58                                                                               9.65 9.96 3.35 3.49                 440                                                                               Linoleic acid                                                                            ##STR241##   225-240/0.08                                                                          69.01                                                                               69.90                                                                               8.69 8.79 3.10 3.32                 441                                                                               Linoleic acid                                                                            ##STR242##   225-234/0.2                                                                           67.52                                                                               67.66                                                                               8.72 8.76 3.03 3.27                 442                                                                               Linoleic acid                                                                            ##STR243##   223-238/0.1                                                                           67.52                                                                               67.54                                                                               8.72 8.75 3.03 3.08                 443                                                                               Linoleic acid                                                                            ##STR244##   224-236/0.1                                                                           67.52                                                                               67.68                                                                               8.72 8.82 3.03 3.19                 444                                                                               Linoleic acid                                                                            ##STR245##   218-237/0.09                                                                          68.06                                                                               68.09                                                                               8.82 8.84 2.94 3.05                 445                                                                               Linoleic acid                                                                            ##STR246##   210-224/0.04                                                                          81.55                                                                               81.58                                                                               10.90                                                                               10.94                                                                               3.52 3.58                 446                                                                               Linoleic acid                                                                            ##STR247##   217-220/0.08                                                                          74.69                                                                               74.73                                                                               9.65 9.83 3.35 3.50                 447                                                                               Linoleic acid                                                                            ##STR248##   217-226/0.08                                                                          74.69                                                                               74.63                                                                               9.65 9.70 3.35 3.25                 448                                                                               Linoleic acid                                                                            ##STR249##   220-223/0.09                                                                          78.40                                                                               78.29                                                                               10.48                                                                               10.34                                                                               3.39 3.38                 449                                                                               Linoleic acid                                                                            ##STR250##   209-223/0.09                                                                          78.40                                                                               78.38                                                                               10.48                                                                               10.33                                                                               3.39 3.29                 450                                                                               Linoleic acid                                                                            ##STR251##   218-223/0.1                                                                           78.40                                                                               78.37                                                                               10.48                                                                               10.37                                                                               3.39 3.24                 451                                                                               Oleic acid                                                                               ##STR252##   212-222/0.08                                                                          81.29                                                                               81.31                                                                               11.45                                                                               11.45                                                                               3.39 3.54                 452                                                                               Oleic acid                                                                               ##STR253##   212-223/0.09                                                                          81.44                                                                               81.56                                                                               11.55                                                                               11.59                                                                               3.28 3.56                 453                                                                               Oleic acid                                                                               ##STR254##   224-231/0.09                                                                          67.24                                                                               67.34                                                                               9.05 8.94 3.01 3.29                 454                                                                               Isostearic acid                                                                          ##STR255##   202-217/0.08                                                                          80.73                                                                               80.74                                                                               11.83                                                                               12.92                                                                               3.49 3.52                 455                                                                               Isostearic acid                                                                          ##STR256##   208-231/0.1                                                                           81.33                                                                               81.42                                                                               12.11                                                                               12.22                                                                               3.06 3.18                 456                                                                               Isostearic acid                                                                          ##STR257##   221-228/0.09                                                                          74.02                                                                               74.23                                                                               10.43                                                                               10.56                                                                               3.32 3.41                 457                                                                               Isostearic acid                                                                          ##STR258##   223-241/0.1                                                                           66.95                                                                               67.04                                                                               9.44 9.58 3.00 3.20                 458                                                                               Isostearic acid                                                                          ##STR259##   220-224/0.05                                                                          77.64                                                                               77.64                                                                               11.34                                                                               11.45                                                                               3.35 3.25                 459                                                                               Isostearic acid                                                                          ##STR260##   220-230/0.09                                                                          78.14                                                                               78.24                                                                               11.53                                                                               11.55                                                                               3.14 3.09                 460                                                                               Linolenic acid                                                                           ##STR261##   220-237/0.08                                                                          79.61                                                                               79.73                                                                               10.18                                                                               10.34                                                                               3.29 3.33                 461                                                                               Linolenic acid                                                                           ##STR262##   215-229/0.1                                                                           79.61                                                                               79.77                                                                               10.18                                                                               10.32                                                                               3.29 3.40                 462                                                                               Linolenic acid                                                                           ##STR263##   221-242/0.09                                                                          81.97                                                                               82.04                                                                               10.45                                                                               10.65                                                                               3.54 3.48                 463                                                                               Linolenic acid                                                                           ##STR264##   217-238/0.2                                                                           75.09                                                                               75.19                                                                               9.14 10.07                                                                               3.36 3.37                 464                                                                               Linseed oil acid                                                                         ##STR265##   199-218/0.09                                         465                                                                               Linseed oil acid                                                                         ##STR266##   222-228/0.08                                         466                                                                               Safflower oil acid                                                                       ##STR267##   204-209/0.06                                         467                                                                               Safflower oil acid                                                                       ##STR268##   203-212/0.06                                         468                                                                               Safflower oil acid                                                                       ##STR269##   219-229/0.06                                         469                                                                               Safflower oil acid                                                                       ##STR270##   220-224/0.1                                          470                                                                               Soybean oil acid                                                                         ##STR271##   219-235/0.06                                         471                                                                               Sunflower oil acid                                                                       ##STR272##   220-240/0.05                                         472                                                                               Castor oil acid                                                                          ##STR273##   217-227/0.06                                         473                                                                               Rape-seed oil acid                                                                       ##STR274##   220-226/0.06                                         474                                                                               Cottonseed oil acid                                                                      ##STR275##   222-229/0.05                                         475                                                                               Olive oil acid                                                                           ##STR276##   215-227/0.05                                         476                                                                               Peanut oil acid                                                                          ##STR277##   220-225/0.05                                         477                                                                               Locust oil acid                                                                          ##STR278##   222-226/0.06                                         478                                                                               Chrysalis oil acid                                                                       ##STR279##   231-240/0.05                                         479                                                                               Shark oil acid                                                                           ##STR280##   223-240/0.05                                         480                                                                               Sardine oil acid                                                                         ##STR281##   217-231/0.05                                         481                                                                               Mackerel oil acid                                                                        ##STR282##   220-225/0.06                                         482                                                                               Herring oil acid                                                                         ##STR283##   195-220/0.06                                         483                                                                               Saurel oil acid                                                                          ##STR284##   201-230/0.05                                         484                                                                               Cod oil acid                                                                             ##STR285##   200-225/0.04                                         485                                                                               Gray mullet oil acid                                                                     ##STR286##   196-236/0.05                                         486                                                                               Menhaden oil acid                                                                        ##STR287##   181-241/0.06                                         487                                                                               Flatfish oil acid                                                                        ##STR288##   195-240/0.08                                         488                                                                               Residual oil acid                                                                        ##STR289##   204-235/0.05                                         __________________________________________________________________________

    __________________________________________________________________________                                        C %      H %      N %                       Example                            Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-               No. Acid moiety                                                                               Amine moiety                                                                               n.sub.D tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical                __________________________________________________________________________     489 Linoleic acid                                                                              ##STR290## 23°C.                                                                       1.5111                                                                             72.86                                                                               72.93                                                                              9.41 9.60                                                                               6.54 6.49                 490 Oleic acid                                                                                 ##STR291## 22°C.                                                                       1.5124                                                                             72.93                                                                               73.06                                                                              9.97 10.03                                                                              6.30 6.25                 491 Linolenic acid                                                                             ##STR292## 23°C.                                                                       1.5100                                                                             73.60                                                                               73.80                                                                              9.15 9.30                                                                               6.36 6.24                 492 Linoleic acid                                                                              ##STR293## 23°C.                                                                       1.5154                                                                             73.26                                                                               73.32                                                                              9.56 9.52                                                                               6.33 6.24                 493 Linoleic acid                                                                              ##STR294## 26°C.                                                                       1.5109                                                                             72.86                                                                               72.89                                                                              9.41 9.48                                                                               6.54 6.37                 494 Isostearic acid                                                                            ##STR295## 27°C.                                                                       1.5156                                                                             72.18                                                                               72.24                                                                              10.25                                                                               10.40                                                                              6.48 6.34                 495 Isostearic acid                                                                            ##STR296## 28°C.                                                                       1.5152                                                                             72.18                                                                               72.20                                                                              10.25                                                                               10.36                                                                              6.48 6.34                 496 Safflower oil acid                                                                         ##STR297## 22°C.                                                                       1.5139                                          497 Soybean oil acid                                                                           ##STR298## 20°C.                                                                       1.5131                                          498 Sesame oil acid                                                                            ##STR299## 22°C.                                                                       1.5107                                          499 Castor oil acid                                                                            ##STR300## 22°C.                                                                       1.5122                                          500 Corn oil acid                                                                              ##STR301## 24°C.                                                                       1.5123                                          501 Cottonseed oil acid                                                                        ##STR302## 23°C.                                                                       1.5129                                          502 Olive oil acid                                                                             ##STR303## 25°C.  1.5138                                503 Linseed oil acid                                                                           ##STR304## 28°C.  1.5119                                504 Rape-seed oil acid                                                                         ##STR305## 14.5°C. 15139                                505 Rice bran oil acid                                                                         ##STR306## 18°C.  1.5123                                506 Chrysalis oil acid                                                                         ##STR307## 23°C.  1.5100                                507 Flatfish oil acid                                                                          ##STR308## 22°C.  1.5122                                508 Shark oil acid                                                                             ##STR309## 20°C.  1.5148                                509 Whale oil acid                                                                             ##STR310## 23°C.                                                                       1.5134                                          510 Cuttlefish oil acid                                                                        ##STR311## 28°C.                                                                       1.5120                                          511 Sardine oil acid                                                                           ##STR312## 23°C.                                                                       1.5221                                          512 Mackerel oil acid                                                                          ##STR313## 23°C.                                                                       1.5145                                          513 Saury pike oil acid                                                                        ##STR314## 28°C.                                                                       1.5235                                          514 Herring oil acid                                                                           ##STR315## 30°C.                                                                       1.5114                                          515 Saurel oil acid                                                                            ##STR316## 30°C.                                                                       1.5138                                          516 Menhaden oil acid                                                                          ##STR317## 32°C.                                                                       1.5149                                          517 Cod oil acid                                                                               ##STR318## 32°C.                                                                       1.5130                                          518 Liver oil acid                                                                             ##STR319## 25° C.                                                                      1.5208                                          519 Menuke oil acid                                                                            ##STR320## 21.5°C.                                                                     1.5140                                          520 Residual oil acid                                                                          ##STR321## 20.5°C.                                                                     1.5133                                          __________________________________________________________________________

    __________________________________________________________________________                        ##STR322##                                                                                     C %      H%       N%                        Example                            Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-               No.  Acid moiety  Amine moiety                                                                          Properties                                                                               tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical                __________________________________________________________________________     521  Linoleic acid                                                                                d (+) mp 45°-48°C.                                                               83.60                                                                               83.76                                                                              9.87 10.08                                                                              3.05 3.14                 522  Linoleic acid                                                                                l (-) mp 45°-48°C.                                                               83.60                                                                               83.69                                                                              9.87 10.04                                                                              3.05 3.14                 523  Linoleic acid                                                                               dl (±)                                                                             mp 45°-48°C.                                                               83.60                                                                               83.67                                                                              9.87 10.00                                                                              3.05 3.13                 524  Oleic acid   dl (±)                                                                             Waxy semi solid                                                                          83.24                                                                               83.35                                                                              10.26                                                                               10.32                                                                              3.03 3.14                 525  Isostearic acid                                                                             dl (±)                                                                             "         82.88                                                                               83.04                                                                              10.65                                                                               10.44                                                                              3.02 3.18                 526  Isostearic acid                                                                              d (+) "         82.88                                                                               83.05                                                                              10.65                                                                               10.89                                                                              3.02 3.08                 527  Isostearic acid                                                                              l (-) "         82.88                                                                               83.06                                                                              10.65                                                                               10.67                                                                              3.02 3.08                 528  Linolenic aid                                                                               dl (±)                                                                             "         83.97                                                                               84.12                                                                              9.47  9.73                                                                              3.06 3.22                 529  Linseed oil fatty acid                                                                      dl (±)                                                                             "                                                     530  Safflower oil fatty acid                                                                     d (+) "                                                     531  Safflower oil fatty acid                                                                     l (-) "                                                     532  Safflower oil fatty acid                                                                    dl (±)                                                                             "                                                     533  Soybean oil acid                                                                            dl (±)                                                                             "                                                     534  Sunflower oil acid                                                                          dl (±)                                                                             "                                                     535  Castor oil acid                                                                             "      "                                                     536  Rape-seed oil acid                                                                          "      "                                                     537  Cottonseed oil acid                                                                         "      "                                                     538  Olive oil acid                                                                              "      "                                                     539  Peanut oil acid                                                                             "      "                                                     540  Locust oil acid                                                                             "      "                                                     541  Chrysalis oil acid                                                                          "      "                                                     542  Shark oil acid                                                                              "      "                                                     543  Sardine oil acid                                                                            "      "                                                     544  Mackerel oil acid                                                                           "      "                                                     545  Herring oil acid                                                                            "      "                                                     546  Saurel oil acid                                                                             "      "                                                     547  Cod oil acid "      "                                                     548  Gray mullet oil acid                                                                        "      "                                                     549  Menhaden oil acid                                                                           "      "                                                     550  Flatfish oil acid                                                                           "      "                                                     551  Residual oil acid                                                                           "      "                                                     __________________________________________________________________________

EXAMPLE 552

A solution of 14 g. of linoleic acid in 30 ml. of ether, a solution of 7 g. of α,β-dimethylbenzylamine in 30 ml. of ether, and a solution of 11 g. of dicyclohexyl carbodiimide in 30 ml. of ether were mixed together at one time, and the mixed solution was allowed to stand overnight at room temperature.

Excess dicyclohexyl carbodiimide was decomposed with 2 cc. of acetic acid, and precipitated dicyclohexylurea was removed by filtration. Subsequently, the filtrate was dissolved in 100 ml. of ether, and the ether solution was washed with 5% hydrochloric acid water, 5% caustic soda water and water, and was then dried, concentrated and distilled to obtain 16.1 g. of a desired product, b.p. 198°-222° C./0.06 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.55          81.76                                               H (%)       10.90          11.02                                               N (%)        3.52           3.82                                               ______________________________________                                    

Examples 553-607 are shown in the following table:

    __________________________________________________________________________                                     Re-                                                                            ac-     C %     H %     N %                                                    tion                                                                              b.p. Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-               Ex.                 B           time                                                                              ° C./                                                                        reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti-              No.                                                                               Acid Amine       BNCNB  Solvent                                                                             (h)                                                                               mmHg cal cal cal cal cal cal                __________________________________________________________________________     553                                                                               Linoleic acid                                                                        ##STR323##                                                                                 ##STR324##                                                                           Ether                                                                               18 203-218/ 0.05                                                                       81.55                                                                              81.66                                                                              10.90                                                                              11.06                                                                              3.52                                                                               3.68               554                                                                               Linoleic acid                                                                        ##STR325##                                                                                 ##STR326##                                                                           Ether                                                                               18 208-221/ 0.04                                                                       81.55                                                                              81.76                                                                              10.90                                                                              11.23                                                                              3.52                                                                               3.71               555                                                                               Linoleic acid                                                                        ##STR327##                                                                                 ##STR328##                                                                           Toluene                                                                             18 199-217/ 0.05                                                                       81.69                                                                              81.37                                                                              11.02                                                                              11.45                                                                              3.40                                                                               3.52               556                                                                               Linoleic  acid                                                                       ##STR329##                                                                                 ##STR330##                                                                           Benzene                                                                             18 220-223/ 0.08                                                                       74.69                                                                              74.79                                                                              9.65                                                                               9.91                                                                               3.35                                                                               3.47               557                                                                               Linoleic acid                                                                        ##STR331##                                                                                 ##STR332##                                                                           Benzene                                                                              5 222-225/ 0.07                                                                       74.69                                                                              74.81                                                                              9.65                                                                               9.93                                                                               3.35                                                                               3.39               558                                                                               Linoleic acid                                                                        ##STR333##                                                                                 ##STR334##                                                                           Benzene                                                                             18 220-225/ 0.08                                                                       74.69                                                                              74.38                                                                              9.65                                                                               9.90                                                                               3.35                                                                               3.59               559                                                                               Linoleic acid                                                                        ##STR335##                                                                                 ##STR336##                                                                           Benzene                                                                              5 225-240/ 0.08                                                                       69.01                                                                              69.88                                                                              8.69                                                                               8.79                                                                               3.10                                                                               3.52               560                                                                               Linoleic acid                                                                        ##STR337##                                                                                 ##STR338##                                                                           Toluene                                                                             20 225-235/ 0.2                                                                        67.52                                                                              67.63                                                                              8.72                                                                               8.76                                                                               3.03                                                                               3.28               561                                                                               Linoleic acid                                                                        ##STR339##                                                                                 ##STR340##                                                                           Dioxane                                                                             11 225-233/ 0.1                                                                        67.52                                                                              67.61                                                                              8.72                                                                               8.77                                                                               3.03                                                                               3.30               562                                                                               Linoleic acid                                                                        ##STR341##                                                                                 ##STR342##                                                                           Ether                                                                                5 221-238/ 0.1                                                                        67.52                                                                              67.70                                                                              8.72                                                                               8.80                                                                               3.03                                                                               3.29               563                                                                               Linoleic acid                                                                        ##STR343##                                                                                 ##STR344##                                                                           Benzene                                                                             20 222-238/ 0.09                                                                       68.06                                                                              68.29                                                                              8.82                                                                               8.94                                                                               2.94                                                                               3.06               564                                                                               Linoleic acid                                                                        ##STR345##                                                                                 ##STR346##                                                                           Benzene                                                                             18 208-221/ 0.04                                                                       81.55                                                                              81.55                                                                              10.90                                                                              10.74                                                                              3.52                                                                               3.68               565                                                                               Linoleic  acid                                                                       ##STR347##                                                                                 ##STR348##                                                                           Chloro- form                                                                        12 220-225/ 0.08                                                                       74.69                                                                              74.83                                                                              9.65                                                                               9.83                                                                               3.35                                                                               3.50               566                                                                               Linoleic acid                                                                        ##STR349##                                                                                 ##STR350##                                                                           Chloro form                                                                         12 221-227/ 0.08                                                                       74.69                                                                              74.83                                                                              9.65                                                                               9.90                                                                               3.35                                                                               3.25               567                                                                               Linoleic acid                                                                        ##STR351##                                                                                 ##STR352##                                                                           Benzene                                                                              5 220-225/ 0.09                                                                       78.40                                                                              78.09                                                                              10.48                                                                              10.31                                                                              3.39                                                                               3.28               568                                                                               Linoleic acid                                                                        ##STR353##                                                                                 ##STR354##                                                                           Toluene                                                                             12 218-223/ 0.09                                                                       78.40                                                                              78.08                                                                              10.48                                                                              10.35                                                                              3.39                                                                               3.29               569                                                                               Linoleic acid                                                                        ##STR355##                                                                                 ##STR356##                                                                           Toluene                                                                             12 220-225/ 0.1                                                                        78.40                                                                              78.07                                                                              10.48                                                                              10.31                                                                              3.39                                                                               3.26               570                                                                               Oleic acid                                                                           ##STR357##                                                                                 ##STR358##                                                                           Benzene                                                                              6 212-222/ 0.08                                                                       81.29                                                                              81.41                                                                              11.45                                                                              11.44                                                                              3.39                                                                               3.51               571                                                                               Oleic acid                                                                           ##STR359##                                                                                 ##STR360##                                                                           Benzene                                                                              3 213-223/ 0.09                                                                       81.44                                                                              81.65                                                                              11.55                                                                              11.69                                                                              3.28                                                                               3.50               572                                                                               Oleic acid                                                                           ##STR361##                                                                                 ##STR362##                                                                           Toluene                                                                              6 226/231/ 0.09                                                                       67.24                                                                              67.44                                                                              9.05                                                                               8.85                                                                               3.01                                                                               3.39               573                                                                               Isostearic acid                                                                      ##STR363##                                                                                 ##STR364##                                                                           Toluene                                                                              8 200-217/ 0.08                                                                       80.73                                                                              80.91                                                                              11.83                                                                              12.03                                                                              3.49                                                                               3.62               574                                                                               Isostearic acid                                                                      ##STR365##                                                                                 ##STR366##                                                                           Ether                                                                               10 209-231/ 0.1                                                                        81.33                                                                              81.52                                                                              12.11                                                                              12.32                                                                              3.06                                                                               3.28               575                                                                               Isostearic acid                                                                      ##STR367##                                                                                 ##STR368##                                                                           Dioxane                                                                             10 221-228/ 0.09                                                                       74.02                                                                              74.33                                                                              10.43                                                                              10.66                                                                              3.32                                                                               3.61               576                                                                               Isostearic acid                                                                      ##STR369##                                                                                 ##STR370##                                                                           Ether                                                                                6 223-241/ 0.1                                                                        66.95                                                                              67.06                                                                              9.44                                                                               9.58                                                                               3.00                                                                               3.21               577                                                                               Isostearic acid                                                                      ##STR371##                                                                                 ##STR372##                                                                           Dioxane                                                                             12 221-226/ 0.05                                                                       77.64                                                                              77.74                                                                              11.34                                                                              11.65                                                                              3.35                                                                               3.15               578                                                                               Isostearic acid                                                                      ##STR373##                                                                                 ##STR374##                                                                           Cyclo- hexane                                                                       12 222-231/ 0.09                                                                       78.14                                                                              78.32                                                                              11.53                                                                              11.58                                                                              3.14                                                                               3.08               579                                                                               Linolenic acid                                                                       ##STR375##                                                                                 ##STR376##                                                                           Ether                                                                               12 220-239/ 0.08                                                                       79.61                                                                              79.93                                                                              10.18                                                                              10.31                                                                              3.29                                                                               3.31               580                                                                               Linolenic acid                                                                       ##STR377##                                                                                 ##STR378##                                                                           Tetra- hydro- furan                                                                 18 218-238/ 0.1                                                                        79.61                                                                              79.78                                                                              10.18                                                                              10.32                                                                              3.29                                                                               3.40               581                                                                               Linolenic acid                                                                       ##STR379##                                                                                 ##STR380##                                                                           Benzene                                                                              6 221-240/ 0.09                                                                       81.97                                                                              82.06                                                                              10.45                                                                              10.65                                                                              3.54                                                                               3.28               582                                                                               Linolenic acid                                                                       ##STR381##                                                                                 ##STR382##                                                                           Benzene                                                                             10 219-239/ 0.2                                                                        75.09                                                                              75.19                                                                              9.14                                                                               10.09                                                                              3.36                                                                               3.67               583                                                                               Linseed oil acid                                                                     ##STR383##                                                                                 ##STR384##                                                                           Benzene                                                                             10 199-219/ 0.09                               584                                                                               Linseed oil acid                                                                     ##STR385##                                                                                 ##STR386##                                                                           Benzene                                                                             10 220-230/ 0.08                               585                                                                               Safflower oil acid                                                                   ##STR387##                                                                                 ##STR388##                                                                           Benzene                                                                              5 203-209/ 0.06                               586                                                                               Safflower oil acid                                                                   ##STR389##                                                                                 ##STR390##                                                                           Benzene                                                                             10 203-211/ 0.06                               587                                                                               Safflower oil acid                                                                   ##STR391##                                                                                 ##STR392##                                                                           Ether                                                                               10 219-228/ 0.06                               588                                                                               Safflower oil acid                                                                   ##STR393##                                                                                 ##STR394##                                                                           Ether                                                                                4 220-226/ 0.1                                589                                                                               Soybean oil acid                                                                     ##STR395##                                                                                 ##STR396##                                                                           Ether                                                                                4 219-237/ 0.06                               590                                                                               Sunflower oil acid                                                                   ##STR397##                                                                                 ##STR398##                                                                           Toluene                                                                              4 222-241/ 0.05                               591                                                                               Castor oil acid                                                                      ##STR399##                                                                                 ##STR400##                                                                           Benzene                                                                              5 218-228/ 0.01                               592                                                                               Rape seed oil                                                                        ##STR401##                                                                                 ##STR402##                                                                           Toluene                                                                              8 221-228/ 0.04                               593                                                                               Cottonseed oil acid                                                                  ##STR403##                                                                                 ##STR404##                                                                           Ether                                                                               10 223-231/ 0.05                               594                                                                               Olive oil acid                                                                       ##STR405##                                                                                 ##STR406##                                                                           Benzene                                                                             10 214-229/ 0.05                               595                                                                               Peanut oil acid                                                                      ##STR407##                                                                                 ##STR408##                                                                           Benzene                                                                             12 220-227/ 0.06                               596                                                                               Locust oil acid                                                                      ##STR409##                                                                                 ##STR410##                                                                           Dioxane                                                                             12 223-227/ 0.06                               597                                                                               Chrysalis oil acid                                                                   ##STR411##                                                                                 ##STR412##                                                                           Chloro- form                                                                        18 233-242/ 0.05                               598                                                                               Shark oil acid                                                                       ##STR413##                                                                                 ##STR414##                                                                           Toluene                                                                             10 225-241/ 0.05                               599                                                                               Sardine oil acid                                                                     ##STR415##                                                                                 ##STR416##                                                                           Tetra- hydro- furan                                                                  5 218-232/ 0.05                               600                                                                               Mackerel oil acid                                                                    ##STR417##                                                                                 ##STR418##                                                                           Dioxane                                                                             18 221-227/ 0.06                               601                                                                               Herring oil acid                                                                     ##STR419##                                                                                 ##STR420##                                                                           Acetone                                                                              5 193-223/ 0.07                               602                                                                               Saurel oil acid                                                                      ##STR421##                                                                                 ##STR422##                                                                           Ether                                                                               10 202-231/ 0.06                               603                                                                               Cod oil acid                                                                         ##STR423##                                                                                 ##STR424##                                                                           Benzene                                                                             20 199-227/ 0.05                               604                                                                               Gray mullet oil acid                                                                 ##STR425##                                                                                 ##STR426##                                                                           Acetone                                                                              5 194-237/ 0.06                               605                                                                               Menhaden oil acid                                                                    ##STR427##                                                                                 ##STR428##                                                                           Ether                                                                                5 181-241/ 0.06                               606                                                                               Flatfish oil acid                                                                    ##STR429##                                                                                 ##STR430##                                                                           Toluene                                                                             18 186-241/ 0.08                               607                                                                               Residual oil acid                                                                    ##STR431##                                                                                 ##STR432##                                                                           Benzene                                                                              4 201-235/ 0.06                               __________________________________________________________________________

EXAMPLE 608

A mixture of 28 g. of linoleic acid and 14 g. of α,p-dimethylbenzylamine, was heated at 180° C. for 20 hours. After separating water the reaction mixture was distilled to obtain 33.3 g. of a desired product, b.p. 119°-219° C./0.05 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.55          81.77                                               H (%)       10.90          11.04                                               N (%)        3.52           3.49                                               ______________________________________                                    

Examples 609-663 are shown in the following table:

    __________________________________________________________________________                          Reac-                                                                          tion                                                                               Reac-                                                                      temp-                                                                              tion       C %      H %      N %                      Ex.                                                                                Acid             erature                                                                            time                                                                               b.p.   Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                            Analy-               No.                                                                               Moiety                                                                              Amine Moiety (° C.)                                                                      (hr.)                                                                              ° C./mmHg                                                                      tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                              tical                __________________________________________________________________________     609                                                                               Linoleic acid                                                                        ##STR433##  200 12  202-219/0.05                                                                          81.55                                                                               81.61                                                                              10.90                                                                               11.02                                                                              3.52                                                                               3.48                 610                                                                               Linoleic  acid                                                                       ##STR434##  200 12  208-220/0.05                                                                          81.55                                                                               81.63                                                                              10.90                                                                               11.03                                                                              3.52                                                                               3.48                 611                                                                               Linoleic  acid                                                                       ##STR435##  180 12  197-209/0.03                                                                          81.69                                                                               81.79                                                                              11.02                                                                               11.05                                                                              3.40                                                                               3.31                 612                                                                               Linoleic acid                                                                        ##STR436##  180 20  220-223/0.07                                                                          74.69                                                                               74.81                                                                               9.65                                                                                9.88                                                                              3.33                                                                               3.27                 613                                                                               Linoleic acid                                                                        ##STR437##  180 24  222-225/0.05                                                                          74.69                                                                               74.83                                                                               9.65                                                                                9.89                                                                              3.35                                                                               3.19                 614                                                                               Linoleic acid                                                                        ##STR438##  175 21  219-224/0.05                                                                          74.69                                                                               74.84                                                                               9.65                                                                                9.84                                                                              3.35                                                                               3.28                 615                                                                               Linoleic acidi                                                                       ##STR439##  200 20  223-241/0.08                                                                          69.01                                                                               69.23                                                                               8.69                                                                                8.74                                                                              3.10                                                                               3.30                 616                                                                               Linoleic acid                                                                        ##STR440##  175 21  225-240/0.2                                                                           67.52                                                                               67.77                                                                               8.72                                                                                8.79                                                                              3.03                                                                               3.45                 617                                                                               Linoleic acid                                                                        ##STR441##  200 12  222-238/0.1                                                                           67.52                                                                               67.71                                                                               8.72                                                                                8.83                                                                              3.03                                                                               3.40                 618                                                                               Linoleic acid                                                                        ##STR442##  200 12  220-237/0.09                                                                          67.52                                                                               67.74                                                                               8.72                                                                                8.85                                                                              3.03                                                                               3.21                 619                                                                               Linoleic acid                                                                        ##STR443##  175 21  222-234/0.08                                                                          68.06                                                                               68.31                                                                               8.82                                                                                8.90                                                                              2.94                                                                               3.08                 620                                                                               Linoleic acid                                                                        ##STR444##  180 12  208-224/0.05                                                                          81.55                                                                               81.69                                                                              10.90                                                                               10.98                                                                              3.52                                                                               3.72                 621                                                                               Linoleic acid                                                                        ##STR445##  175 12  220-225/0.06                                                                          74.69                                                                               74.81                                                                               9.65                                                                                9.92                                                                              3.35                                                                               3.45                 622                                                                               Linoleic acid                                                                        ##STR446##  180 12  221-225/0.08                                                                          74.69                                                                               74.83                                                                               9.65                                                                                9.90                                                                              3.35                                                                               3.61                 623                                                                               Linoleic acid                                                                        ##STR447##  175 21  220-224/0.08                                                                          78.40                                                                               78.85                                                                              10.48                                                                               10.63                                                                              3.39                                                                               3.29                 624                                                                               Linoleic acid                                                                        ##STR448##  180 18  218-230/0.1                                                                           78.40                                                                               78.59                                                                              10.48                                                                               10.61                                                                              3.39                                                                               3.71                 625                                                                               Linoleic acid                                                                        ##STR449##  180 13  218-223/0.09                                                                          78.40                                                                               78.58                                                                              10.48                                                                               10.61                                                                              3.39                                                                               3.48                 626                                                                               Oleic acid                                                                           ##STR450##  200 12  208-220/0.08                                                                          81.29                                                                               81.41                                                                              11.45                                                                               11.35                                                                              3.39                                                                               3.09                 627                                                                               Oleic acid                                                                           ##STR451##  200 12  210-225/0.09                                                                          81.44                                                                               81.62                                                                              11.55                                                                               11.36                                                                              3.28                                                                               3.19                 628                                                                               Oleic acid                                                                           ##STR452##  175 20  224-232/0.09                                                                          67.24                                                                               67.41                                                                               9.05                                                                                9.15                                                                              3.01                                                                               3.12                 629                                                                               Isostearic acid                                                                      ##STR453##  175 18  200-215/0.08                                                                          80.73                                                                               80.90                                                                              11.83                                                                               11.94                                                                              3.49                                                                               3.29                 630                                                                               Isostearic acid                                                                      ##STR454##  180 18  209-230/0.09                                                                          81.33                                                                               81.47                                                                              12.11                                                                               12.22                                                                              3.06                                                                               3.15                 631                                                                               Isostearic acid                                                                      ##STR455##  175 18  221-228/0.08                                                                          74.02                                                                               74.33                                                                              10.43                                                                               10.33                                                                              3.32                                                                               3.46                 632                                                                               Isostearic acid                                                                      ##STR456##  200 12  222-243/0.09                                                                          66.95                                                                               67.06                                                                               9.44                                                                                9.60                                                                              3.00                                                                               3.06                 633                                                                               Isostearic acid                                                                      ##STR457##  175 18  222-226/0.05                                                                          77.64                                                                               77.84                                                                              11.34                                                                               11.58                                                                              3.35                                                                               3.39                 634                                                                               Isostearic acid                                                                      ##STR458##  175 18  222-233/0.09                                                                          78.14                                                                               78.20                                                                              11.53                                                                               11.51                                                                              3.14                                                                               3.33                 635                                                                               Linolenic acid                                                                       ##STR459##  175 18  218-241/0.08                                                                          79.61                                                                               79.60                                                                              10.18                                                                               10.36                                                                              3.29                                                                               3.45                 636                                                                               Linolenic acid                                                                       ##STR460##  180 18  216-237/0.1                                                                           79.61                                                                               79.49                                                                              10.18                                                                               10.37                                                                              3.29                                                                               3.45                 637                                                                               Linolenic acid                                                                       ##STR461##  175 21  218-241/0.09                                                                          81.97                                                                               82.08                                                                              10.45                                                                               10.59                                                                              3.54                                                                               3.68                 638                                                                               Linolenic acid                                                                       ##STR462##  150 23  212-222/0.08                                                                          75.09                                                                               84.98                                                                               9.14                                                                                9.34                                                                              3.36                                                                               3.47                 639                                                                               Linseed oil acid                                                                     ##STR463##  220 12  198-228/0.08                                      640                                                                               Linseed oil acid                                                                     ##STR464##  150 24  203-209/0.06                                      641                                                                               Safflower oil acid                                                                   ##STR465##  150 24  203-215/0.07                                      642                                                                               Safflower oil acid                                                                   ##STR466##  175 18  219-228/0.06                                      643                                                                               Safflower oil acid                                                                   ##STR467##  200 12  218-224/0.05                                      644                                                                               Safflower oil acid                                                                   ##STR468##  150 18  220-225/0.1                                       645                                                                               Soybean oil acid                                                                     ##STR469##  200 12  218-234/0.05                                      646                                                                               Sun- flower oil acid                                                                 ##STR470##  170 18  218-225/0.05                                      647                                                                               Castor oil acid                                                                      ##STR471##  170 18  218-225/0.05                                      648                                                                               Rape- seed oil acid                                                                  ##STR472##  200 20  220-228/0.06                                      649                                                                               Cotton- seed oil acid                                                                ##STR473##  175 18  223-231/0.05                                      650                                                                               Olive oil acid                                                                       ##STR474##  150 12  214-229/0.05                                      651                                                                               Peanut oil acid                                                                      ##STR475##  175 12  220-226/0.06                                      652                                                                               Locust oil acid                                                                      ##STR476##  200 12  218-229/0.05                                      653                                                                               Chrysalis oil acid                                                                   ##STR477##  180 12  233-242/0.05                                      654                                                                               Shark oil  acid                                                                      ##STR478##  180 21  225-243/0.05                                      655                                                                               Sardine oil acid                                                                     ##STR479##  175 20  209-228/0.05                                      656                                                                               Mackerel oil acid                                                                    ##STR480##  175 20  218-224/0.05                                      657                                                                               Herring oil acid                                                                     ##STR481##  200 18  194-218/0.06                                      658                                                                               Saurel oil acid                                                                      ##STR482##  180 18  197-230/0.06                                      659                                                                               Cod oil acid                                                                         ##STR483##  175 18  198-219/0.05                                      660                                                                               Gray mullet oil acid                                                                 ##STR484##  175 18  193-240/0.07                                      661                                                                               Men- haden oil acid                                                                  ##STR485##  180 18  183-239/0.06                                      662                                                                               Flatfish oil acid                                                                    ##STR486##  175 18  194-237/0.08                                      663                                                                               Residual oil acid                                                                    ##STR487##  200 18  201-230/0.06                                      __________________________________________________________________________

EXAMPLE 664

To a mixture of 13.5 g. of α,p-dimethylbenzylamine, 7 g. of trimethylamine and 100 ml. of anhydrous ether was added a solution of 29.9 g. of linoleic acid chloride in 50 ml. of anhydrous ether under cooling and stirring at 0° - 5° C. After addition, the reaction mixture was boiled for 2 hours and the ether solution was washed with acid, alkoli and water, and was then dried, concentrated and distilled to obtain 38 g. of a desired product. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.55          81.69                                               H (%)       10.90          11.12                                               N (%)        3.52           3.44                                               ______________________________________                                    

Examples 665-719 are shown in the following table, in which:

Solvent:

a. Ether

b. Dioxane

c. Tetrahydrofuran

d. Acetone

e. Methylisobutylketone

f. Benzene

g. Toluene

h. Chloroform

i. Dimethylformamide

k. Water

    __________________________________________________________________________                                             C %     H %     N                      __________________________________________________________________________                                                             %                                           Conden-            Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                  Acid              sing     Sol-                                                                              b.p.   reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti-              Ex.                                                                               Moiety                                                                              Amine Moiety agent    vent                                                                              ° C/mmHg                                                                       cal cal cal cal cal cal                __________________________________________________________________________     665                                                                               Linoleic acid chloride                                                               ##STR488##  K.sub.2 CO.sub.3                                                                        d  200-216/0.02                                                                          81.55                                                                              81.67                                                                              10.90                                                                              10.99                                                                              3.52                                                                               3.40               666                                                                               Linoleic acid chloride                                                               ##STR489##  NaOH     k,d                                                                               208-221/0.05                                                                          81.55                                                                              81.71                                                                              10.90                                                                              11.13                                                                              3.52                                                                               3.42               667                                                                               Linoleic acid chloride                                                               ##STR490##  K.sub.2 CO.sub.3                                                                        d  200-209/0.03                                                                          81.69                                                                              81.90                                                                              11.02                                                                              11.25                                                                              3.40                                                                               3.19               668                                                                               Linoleic acid chloride                                                               ##STR491##  Na.sub.2 CO.sub.3                                                                       e  215-221/0.06                                                                          74.69                                                                              74.82                                                                               9.65                                                                               9.83                                                                              3.35                                                                               3.09               669                                                                               Linoleic acid chloride                                                               ##STR492##                                                                                  ##STR493##                                                                             a  220-228/0.05                                                                          74.69                                                                              74.85                                                                               9.65                                                                               9.84                                                                              3.35                                                                               3.12               670                                                                               Linoleic acid chloride                                                               ##STR494##                                                                                  ##STR495##                                                                             a  216-223/0.06                                                                          74.69                                                                              74.84                                                                               9.65                                                                               9.87                                                                              3.35                                                                               3.11               671                                                                               Linoleic acid chloride                                                               ##STR496##  NaOH     k,b                                                                               218-239/0.06                                                                          69.01                                                                              69.22                                                                               8.69                                                                               8.81                                                                              3.10                                                                               2.94               672                                                                               Linoleic acid chloride                                                               ##STR497##  NaOH     d  221-236/0.08                                                                          67.52                                                                              67.78                                                                               8.72                                                                               8.90                                                                              3.03                                                                               2.90               673                                                                               Linoleic acid chloride                                                               ##STR498##                                                                                  ##STR499##                                                                             f  218-229/0.09                                                                          67.52                                                                              67.76                                                                               8.72                                                                               8.92                                                                              3.03                                                                               2.87               674                                                                               Linoleic acid chloride                                                               ##STR500##  K.sub.2 CO.sub.3                                                                        d  218-235/0.08                                                                          67.52                                                                              67.71                                                                               8.72                                                                               8.97                                                                              3.03                                                                               2.88               675                                                                               Linoleic acid chloride                                                               ##STR501##                                                                                  ##STR502##                                                                             f  216-233/0.07                                                                          68.06                                                                              68.31                                                                               8.82                                                                               8.99                                                                              2.94                                                                               2.67               676                                                                               Linoleic acid chloride                                                               ##STR503##  NaOH     k,c                                                                               208-222/0.05                                                                          81.55                                                                              81.70                                                                              10.90                                                                              11.05                                                                              3.52                                                                               3.42               677                                                                               Linoleic acid chloride                                                               ##STR504##  K.sub.2 CO.sub.3                                                                        e  218-223/0.06                                                                          74.69                                                                              74.75                                                                               9.65                                                                               9.78                                                                              3.55                                                                               3.02               678                                                                               Linoleic acid chloride                                                               ##STR505##  NaOH     k,b                                                                               217-227/0.05                                                                          74.69                                                                              74.82                                                                               9.65                                                                               9.92                                                                              3.35                                                                               3.11               679                                                                               Linoleic acid chloride                                                               ##STR506##                                                                                  ##STR507##                                                                             e  219-229/0.05                                                                          78.40                                                                              78.70                                                                              10.48                                                                              10.72                                                                              3.39                                                                               3.18               680                                                                               Linoleic acid chloride                                                               ##STR508##                                                                                  ##STR509##                                                                             e  218-232/0.08                                                                          78.40                                                                              78.62                                                                              10.48                                                                              10.74                                                                              3.39                                                                               3.29               681                                                                               Linoleic acid chloride                                                               ##STR510##  NaOH     k,i                                                                               216-229/0.07                                                                          78.40                                                                              78.62                                                                              10.48                                                                              10.69                                                                              3.39                                                                               3.19               682                                                                               Oleic acid                                                                           ##STR511##  NaOH     k,b                                                                               206-221/0.06                                                                          81.29                                                                              81.42                                                                              11.45                                                                              11.65                                                                              3.39                                                                               3.19               683                                                                               Oleic acid chloride                                                                  ##STR512##  NaOH     k,b                                                                               208-225/0.08                                                                          81.44                                                                              81.51                                                                              11.55                                                                              11.62                                                                              3.28                                                                               3.08               684                                                                               Oleic acid chloride                                                                  ##STR513##  K.sub.2 CO.sub.3                                                                        d  223-235/0.06                                                                          67.24                                                                              67.39                                                                               9.05                                                                               9.23                                                                              3.01                                                                               2.89               685                                                                               Isostearic acid chloride                                                             ##STR514##  NaOH     k,d                                                                               200-215/0.08                                                                          80.73                                                                              80.88                                                                              11.83                                                                              11.96                                                                              3.49                                                                               3.29               686                                                                               Isostearic acid chloride                                                             ##STR515##                                                                                  ##STR516##                                                                             f  209-230/0.08                                                                          81.33                                                                              81.42                                                                              12.11                                                                              12.35                                                                              3.06                                                                               2.94               687                                                                               Isostearic acid chloride                                                             ##STR517##                                                                                  ##STR518##                                                                             f  220-227/0.05                                                                          74.02                                                                              74.22                                                                              10.43                                                                              10.65                                                                              3.32                                                                               3.16               688                                                                               Isostearic acid chloride                                                             ##STR519##                                                                                  ##STR520##                                                                             a  218-242/0.07                                                                          66.95                                                                              66.99                                                                               9.44                                                                               9.61                                                                              3.00                                                                               2.93               689                                                                               Isostearic acid chloride                                                             ##STR521##  NaOH     k,d                                                                               217-227/0.05                                                                          77.64                                                                              77.81                                                                              11.34                                                                              11.51                                                                              3.35                                                                               3.16               690                                                                               Isostearic acid chloride                                                             ##STR522##                                                                                  ##STR523##                                                                             a  219-231/0.08                                                                          78.14                                                                              78.32                                                                              11.53                                                                              11.68                                                                              3.14                                                                               3.07               691                                                                               Linolenic acid chloride                                                              ##STR524##                                                                                  ##STR525##                                                                             a  218-240/0.07                                                                          79.61                                                                              79.79                                                                              10.18                                                                              10.31                                                                              3.29                                                                               3.08               692                                                                               Linolenic acid chloride                                                              ##STR526##                                                                                  ##STR527##                                                                             d  212-225/0.07                                                                          79.61                                                                              79.77                                                                              10.18                                                                              10.30                                                                              3.29                                                                               3.08               693                                                                               Linolenic acid chloride                                                              ##STR528##                                                                                  ##STR529##                                                                             a  200-225/0.05                                                                          81.97                                                                              82.23                                                                              10.45                                                                              10.58                                                                              3.54                                                                               3.19               694                                                                               Linolenic acid chloride                                                              ##STR530##                                                                                  ##STR531##                                                                             e  201-212/0.03                                                                          75.05                                                                              75.24                                                                               9.14                                                                               9.32                                                                              3.36                                                                               3.26               695                                                                               Linseed oil acid chloride                                                            ##STR532##  NaOH     a  203-215/0.07                                  696                                                                               Linseed oil acid chloride                                                            ##STR533##  NaOH     k,b                                                                               219-228/0.05                                  697                                                                               Safflower oil acid chloride                                                          ##STR534##  NaOH     k,i                                                                               218-233/0.05                                  698                                                                               Safflower oil acid chloride                                                          ##STR535##  NaOH     k,b                                                                               218-228/0.05                                  699                                                                               Safflower oil acid chloride                                                          ##STR536##  K.sub.2 CO.sub.3                                                                        e  218-226/0.05                                  700                                                                               Safflower oil acid chloride                                                          ##STR537##  K.sub.2 CO.sub.3                                                                        e  220-231/0.08                                  701                                                                               Soybean oil acid chloride                                                            ##STR538##                                                                                  ##STR539##                                                                             f  216-233/0.05                                  702                                                                               Sun- flower oil acid chloride                                                        ##STR540##                                                                                  ##STR541##                                                                             f  215- 236/0.05                                 703                                                                               Castor oil acid chloride                                                             ##STR542##  NaOH     k,c                                                                               214-226/0.05                                  704                                                                               Rape- seed oil acid chloride                                                         ##STR543##  NaOH     k,b                                                                               219-229/0.05                                  705                                                                                ##STR544##                                                                          ##STR545##  K.sub.2 CO.sub.3                                                                        k,d                                                                               223-234/0.05                                  706                                                                               Olive oil acid chloride                                                              ##STR546##  K.sub.2 CO.sub.3                                                                        d  215-232/0.05                                  707                                                                               Peanut oil acid chloride                                                             ##STR547##                                                                                  ##STR548##                                                                             g  219-227/0.06                                  708                                                                               Locust oil acid chloride                                                             ##STR549##                                                                                  ##STR550##                                                                             a  218-227/0.06                                  709                                                                               Chrysalis oil acid chloride                                                          ##STR551##                                                                                  ##STR552##                                                                             c  233-245/0.06                                  710                                                                               Shark oil acid chloride                                                              ##STR553##                                                                                  ##STR554##                                                                             i  228-241/0.05                                  711                                                                               Sardine oil acid chloride                                                            ##STR555##  K.sub.2 CO.sub.3                                                                        d  209-228/0.05                                  712                                                                               Mackerel oil acid chloride                                                           ##STR556##  KOH      k,b                                                                               218-224/0.05                                  713                                                                               Herring oil acid chloride                                                            ##STR557##  KOH      k,c                                                                               194-219/0.05                                  714                                                                               Saurel oil acid chloride                                                             ##STR558##                                                                                  ##STR559##                                                                             h  199-238/0.05                                  715                                                                               Cod oil acid chloride                                                                ##STR560##                                                                                  ##STR561##                                                                             g  198-224/0.05                                  716                                                                               Gray mullet oil acid chloride                                                        ##STR562##                                                                                  ##STR563##                                                                             f  193-242/0.05                                  717                                                                               Men- haden oil acid chloride                                                         ##STR564##  K.sub.2 CO.sub.3                                                                        e  183-239/0.05                                  718                                                                               Flatfish oil acid chloride                                                           ##STR565##  K.sub.2 CO.sub.3                                                                        e  199-235/0.05                                  719                                                                               Residual oil acid chloride                                                           ##STR566##  NaOH     d  200-233/0.05                                  __________________________________________________________________________

EXAMPLE 720

A mixture of 14.9 g. of methyl linoleate and 10 g. of α,p-dimethylbenzylamine was heated at 180° C. for 12 hours removing methanol during the reaction. After completion of the reaction, the reaction mixture was dissolved in 200 ml. of ether and was washed with 5% hydrochloric acid aqueous solution to recover about 2 g. of excess amine. The ether layer washed with water, dried and distilled to obtain 18.9 g. of a desired product. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.55          81.58                                               H (%)       10.90          10.99                                               N (%)        3.52           3.49                                               ______________________________________                                    

Examples 721-800 are shown in the following table:

    __________________________________________________________________________                                             Reac-                                                                          tion Reac-                                                                     tempe-                                                                              tion                              Exam-                                                                               Ester or RCOOA               Catal-                                                                               rature                                                                              time                              ple  glyceride                                                                               A     Amine Moiety  yst   ° C                                                                          (hr) ° C/mmHg.             __________________________________________________________________________     721  Linoleic acid                                                                           CH.sub.3                                                                              ##STR567##   NaOCH.sub.3                                                                          150   4   200-215/0.02                 722  Linoleic acid                                                                           CH.sub.3                                                                              ##STR568##   --    175  18   208-223/0.05                 723  Linoleic acid                                                                           CH.sub.3                                                                              ##STR569##   --    180  12   201-209/0.03                 724  Linoleic acid                                                                           CH.sub.3                                                                              ##STR570##   --    180  12   213-221/0.06                 725  Linoleic acid                                                                           C.sub.2 H.sub.5                                                                       ##STR571##   --    180  12   221-227/0.05                 726  Linoleic acid                                                                           CH.sub.3                                                                              ##STR572##   --    180  12   217-231/0.06                 727  Linoleic acid                                                                           CH.sub.3                                                                              ##STR573##   --    180  12   218-239/0.06                 728  Linoleic acid                                                                           CH.sub.3                                                                              ##STR574##   --    175  14   218-233/0.07                 729  Linoleic acid                                                                           CH.sub.3                                                                              ##STR575##   --    175  14   216-229/0.07                 730  Linoleic acid                                                                           CH.sub.3                                                                              ##STR576##   --    175  14   216-232/0.08                 731  Linoleic acid                                                                           CH.sub.3                                                                              ##STR577##   --    175  14   214-234/0.07                 732  Linoleic acid                                                                           C.sub.2 H.sub.5                                                                       ##STR578##   --    175  14   205-224/0.05                 733  Linoleic acid                                                                           CH.sub.3                                                                              ##STR579##   --    175  14   216-229/0.06                 734  Linoleic acid                                                                           CH.sub.3                                                                              ##STR580##   --    175  14   215-227/0.05                 735  Linoleic acid                                                                           CH.sub.3                                                                              ##STR581##   NaOCH.sub.3                                                                          140   4   219-231/0.05                 736  Linoleic acid                                                                           CH.sub.3                                                                              ##STR582##   --    175  12   217-232/0.08                 737  Linoleic acid                                                                           CH.sub.3                                                                              ##STR583##   KOCH.sub.3                                                                           150   4   216-229/0.07                 738  Oleic acid                                                                              CH.sub.3                                                                              ##STR584##   --    145  21   205-221/0.06                 739  Oleic acid                                                                              CH.sub.3                                                                              ##STR585##   NaOEt 135   4   207-222/0.07                 740  Oleic acid                                                                              CH.sub.3                                                                              ##STR586##   --    160  20   219-233/0.06                 741  Isostearic acid                                                                         CH.sub.3                                                                              ##STR587##   --    165  18   199-221/0.07                 742  Isostearic acid                                                                         CH.sub.3                                                                              ##STR588##   --    175  18   205-230/0.07                 743  Isostearic acid                                                                         CH.sub.3                                                                              ##STR589##   --    175  16   230-234/0.05                 744  Isostearic acid                                                                         CH.sub.3                                                                              ##STR590##   --    175  16   218-238/0.05                 745  Isostearic acid                                                                         CH.sub.3                                                                              ##STR591##   --    175  16   217- 228/0.05                746  Isostearic acid                                                                         C.sub.2 H.sub.5                                                                       ##STR592##   --    175  16   219-233/0.06                 747  Linolenic acid                                                                          CH.sub.3                                                                              ##STR593##   --    180  16   218-238/0.06                 748  Linolenic acid                                                                          CH.sub.3                                                                              ##STR594##   --    180  16   210-225/0.06                 749  Linolenic acid                                                                          CH.sub.3                                                                              ##STR595##   --    180  16   202-222/0.05                 750  Linolenic acid                                                                          CH.sub.3                                                                              ##STR596##   --    160  21   200-212/0.03                 751  Linseed oil acid                                                                        CH.sub.3                                                                              ##STR597##   --    155  21   203-216/0.06                 752  Linseed oil acid                                                                        CH.sub.3                                                                              ##STR598##   --    160  20   218-232/0.05                 753  Safflower oil acid                                                                      CH.sub.3                                                                              ##STR599##   --    160  20   218-241/0.05                 754  Safflower oil acid                                                                      CH.sub.3                                                                              ##STR600##   --    160  18   215-229/0.05                 755  Safflower oils acid                                                                     CH.sub.3                                                                              ##STR601##   --    160  18   215-230/0.05                 756  Safflower oil acid                                                                      CH.sub.3                                                                              ##STR602##   --    160  18   220-241/0.05                 757  Soybean oil acid                                                                        CH.sub.3                                                                              ##STR603##   --    175  18   215-231/0.05                 758  Sunflower oil acid                                                                      CH.sub.3                                                                              ##STR604##   --    180  12   209-233/0.05                 759  Castor oil acid                                                                         CH.sub.3                                                                              ##STR605##   --    180  14   212-228/0.05                 760  Rape-seed oil acid                                                                      CH.sub.3                                                                              ##STR606##   KOtBu 145   4   213-228/0.05                 761  Cottonseed oil acid                                                                     CH.sub.3                                                                              ##STR607##   --    180  12   220-234/0.05                 762  Olive oil acid                                                                          CH.sub.3                                                                              ##STR608##   --    180  12   215-236/0.05                 763  Peanut oil acid                                                                         CH.sub.3                                                                              ##STR609##   --    180  12   219-229/0.03                 764  Locust oil acid                                                                         CH.sub.3                                                                              ##STR610##   --    180  12   219-231/0.06                 765  Chrysalis oil acid                                                                      CH.sub.3                                                                              ##STR611##   --    175  14   229-245/0.06                 766  Shark oil acid                                                                          CH.sub.3                                                                              ##STR612##   --    180  12   228-241/0.05                 767  Sardine oil acid                                                                        CH.sub.3                                                                              ##STR613##   --    175  14   209-231/0.05                 768  Mackerel oil acid                                                                       CH.sub.3                                                                              ##STR614##   --    180  12   216-227/0.05                 769  Herring oil acid                                                                        CH.sub.3                                                                              ##STR615##   NaOEt 135   5   194-219/0.05                 770  Saurel oil acid                                                                         CH.sub.3                                                                              ##STR616##   --    200  10   201-241/0.05                 771  Cod oil acid                                                                            CH.sub.3                                                                              ##STR617##   --    210   8   199-225/0.05                 772  Gray mullet oil acid                                                                    CH.sub.3                                                                              ##STR618##   --    165  16   195-240/0.05                 773  Menhaden oil acid                                                                       CH.sub.3                                                                              ##STR619##   --    160  18   183-239/0.05                 774  Flatfish oil acid                                                                       CH.sub.3                                                                              ##STR620##   --    150  18   202-240/0.05                 775  Residual oil acid                                                                       CH.sub.3                                                                              ##STR621##   --    145  20   200-235/0.05                 776  Linseed oil                                                                                    ##STR622##   --    180  16   194-218/0.06                 777  Linseed oil                                                                                    ##STR623##   --    180  16   200-232/0.05                 778  Safflower oil                                                                                  ##STR624##   NaOCH.sub.3                                                                          140   4   199-239/0.04                 779  Safflower oil                                                                                  ##STR625##   H.sub.3 BO.sub.4                                                                     145  10   202-231/0.05                 780  Safflower oil                                                                                  ##STR626##   --    175  10   200-240/0.05                 781  Safflower oil                                                                                  ##STR627##   --    175  12   203-235/0.05                 782  Soybean oil                                                                                    ##STR628##   --    170  21   198-233/0.05                 783  Sunflower oil                                                                                  ##STR629##   --    175  21   199-235/0.05                 784  Castor oil                                                                                     ##STR630##   --    175  21   202-239/0.05                 785  Rape-seed oil                                                                                  ##STR631##   --    175  22   200-228/0.05                 786  Cottonseed oil                                                                                 ##STR632##   --    175  23   208-235/0.05                 787  Olive oil                                                                                      ##STR633##   --    175  21   200-236/0.04                 788  Peanut oil                                                                                     ##STR634##   --    180  22   200-234/0.05                 789  Locust oil                                                                                     ##STR635##   --    160  22   200-233/0.06                 790  Chrysalis oil                                                                                  ##STR636##   --    145  21   198-244/0.05                 791  Shark oil                                                                                      ##STR637##   --    155  20   212-242/0.05                 792  Sardine oil                                                                                    ##STR638##   H.sub.3 BO.sub.4                                                                     150   4   200-233/0.05                 793  Mackerel oil                                                                                   ##STR639##   --    160  20   198-232/0.04                 794  Herring oil                                                                                    ##STR640##   NaOCH.sub.3                                                                          150   4   190-220/0.05                 795  Saurel oil                                                                                     ##STR641##   --    150  24   194-241/0.04                 796  Cod oil                                                                                        ##STR642##   --    150  24   193-225/0.05                 797  Gray mullet oil                                                                                ##STR643##   --    180  12   195-242/0.05                 798  Menhaden oil                                                                                   ##STR644##   --    210  10   183-241/0.05                 799  Flatfish oil                                                                                   ##STR645##   --    200  10   189-242/0.05                 800  Residual oil                                                                                   ##STR646##   --    180  10   200-235/0.05                 __________________________________________________________________________                                 C %       H %       N %                                                        Theo-                                                                               Ana- Theo-                                                                               Ana- Theo-                                                                               Ana-                                             Exam-                                                                               reti-                                                                               lyti-                                                                               reti-                                                                               lyti-                                                                               reti-                                                                               lyti-                                            ple  cal  cal  cal  cal  cal  cal                       __________________________________________________________________________                            721  81.55                                                                               81.71                                                                               10.98                                                                               10.38                                                                               3.52 3.48                                             722  81.55                                                                               81.77                                                                               10.90                                                                               11.05                                                                               3.52 3.46                                             723  81.69                                                                               81.82                                                                               11.02                                                                               11.40                                                                               3.40 3.19                                             724  74.69                                                                               74.82                                                                                9.65                                                                                9.68                                                                               3.35 3.19                                             725  74.69                                                                               74.81                                                                                9.65                                                                                9.70                                                                               3.35 3.25                                             726  74.69                                                                               74.83                                                                                9.65                                                                                9.77                                                                               3.35 3.26                                             727  69.01                                                                               69.31                                                                                8.69                                                                                8.81                                                                               3.10 3.08                                             728  67.52                                                                               67.72                                                                                8.72                                                                                8.92                                                                               3.03 3.00                                             729  67.52                                                                               67.77                                                                                8.72                                                                                8.89                                                                               3.03 2.98                                             730  67.52                                                                               67.70                                                                                8.72                                                                                8.83                                                                               3.03 2.87                                             731  68.06                                                                               68.31                                                                                8.82                                                                                8.93                                                                               3.94 2.79                                             732  81.55                                                                               81.61                                                                               10.90                                                                               10.94                                                                               3.52 3.32                                             733  74.69                                                                               74.81                                                                                9.65                                                                                9.81                                                                               3.35 3.30                                             734  74.65                                                                               74.79                                                                                9.65                                                                                9.82                                                                               3.35 3.15                                             735  78.40                                                                               78.62                                                                               10.48                                                                               10.62                                                                               3.39 3.19                                             736  78.40                                                                               78.51                                                                               10.48                                                                               10.61                                                                               3.39 3.24                                             737  78.40                                                                               78.51                                                                               10.48                                                                               10.66                                                                               3.39 3.27                                             738  81.29                                                                               81.43                                                                               11.45                                                                               11.64                                                                               3.39 3.36                                             739  81.44                                                                               81.61                                                                               11.55                                                                               11.59                                                                               3.28 3.18                                             740  67.24                                                                               67.44                                                                                9.05                                                                                9.23                                                                               3.01 2.95                                             741  80.73                                                                               80.89                                                                               11.83                                                                               11.93                                                                               3.49 3.34                                             742  81.33                                                                               81.51                                                                               12.11                                                                               12.34                                                                               3.06 2.95                                             743  74.02                                                                               74.11                                                                               10.43                                                                               10.51                                                                               3.32 3.30                                             744  66.95                                                                               67.09                                                                                9.44                                                                                9.61                                                                               3.00 3.01                                             745  77.64                                                                               77.77                                                                               11.34                                                                               11.54                                                                               3.35 3.17                                             746  78.14                                                                               78.31                                                                               11.53                                                                               11.61                                                                               3.14 3.06                                             747  79.61                                                                               79.68                                                                               10.18                                                                               10.31                                                                               3.29 3.20                                             748  79.61                                                                               79.67                                                                               10.18                                                                               10.31                                                                               3.29 3.22                                             749  81.97                                                                               82.03                                                                               10.45                                                                               10.54                                                                               3.54 3.31                                             750  75.09                                                                               75.19                                                                                9.14                                                                                9.23                                                                               3.36 3.08                      __________________________________________________________________________

EXAMPLE 801

A solution of 14 g. of linoleic acid, 7 g. of α,p-dimethylbenzylamine and 0.5 g. of p-toluenesulfonic acid in 100 ml. of toluene, was refluxed for 8 hours using a water separator. The reaction mixture was washed with 5% NaOH aqueous solution, 5% HCl aqueous solution and water and was concentrated, and the residue was distilled to obtain 16.1 g. of a desired product, b.p. 203°-216° C./0.06 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.55          81.71                                               H (%)       10.90          10.99                                               N (%)        3.52           3.42                                               ______________________________________                                    

Examples 802-856 are shown in the following table, in which:

Condensing agent:

A. p-Toluenesulfonic acid.

B. p-Toluenesulfonic acid chloride.

C. sulfuric acid.

D. phenolsulfonic acid.

E. ira-400.

f. amberlist - 15.

Solvent:

a. Toluene.

b. Pyridine.

c. Benzene.

d. Chloroform.

e. Xylene.

f. Tetrachlorocarbon.

    __________________________________________________________________________                                            C %     H %     N %                                                 Reac-      Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                      Ag-                                                                               Sol-                                                                              tion                                                                               b.p.   reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti-               Ex.                                                                                Acid Amine        ent                                                                               vent                                                                              time                                                                               ° C/mmHg.                                                                      cal cal cal cal cal cal                 __________________________________________________________________________     802                                                                               Linoleic acid                                                                         ##STR647##  A  a  8   199-214/0.05                                                                          81.55                                                                              81.67                                                                              10.90                                                                              11.11                                                                              3.52                                                                               3.46                803                                                                               Lineoleic acid                                                                        ##STR648##  A  a  12  203-209/0.04                                                                          81.55                                                                              81.66                                                                              10.90                                                                              11.09                                                                              3.52                                                                               3.48                804                                                                               Linoleic acid                                                                         ##STR649##  A  c  12  199-207/0.04                                                                          81.69                                                                              81.79                                                                              11.02                                                                              11.12                                                                              3.40                                                                               3.22                805                                                                               Linoleic acid                                                                         ##STR650##  A  a  12  220-224/0.07                                                                          74.69                                                                              74.82                                                                              9.65                                                                               9.88                                                                               3.35                                                                               3.16                806                                                                               Linoleic acid                                                                         ##STR651##  A  d  12  219-224/0.06                                                                          74.69                                                                              74.77                                                                              9.65                                                                               9.75                                                                               3.35                                                                               3.25                807                                                                               Linoleic acid                                                                         ##STR652##  B  b  18  216-221/0.05                                                                          74.69                                                                              74.79                                                                              9.65                                                                               9.70                                                                               3.35                                                                               3.19                808                                                                               Linoleic acid                                                                         ##STR653##  A  e  12  220-238/0.06                                                                          69.01                                                                              69.22                                                                              8.69                                                                               8.82                                                                               3.10                                                                               3.01                809                                                                               Linoleic acid                                                                         ##STR654##  D  f  12  215-238/0.09                                                                          67.52                                                                              67.74                                                                              8.72                                                                               8.93                                                                               3.03                                                                               2.98                810                                                                               Linoleic acid                                                                         ##STR655##  C  a  16  222-236/0.1                                                                           67.52                                                                              67.82                                                                              8.72                                                                               8.90                                                                               3.03                                                                               2.94                811                                                                               Linoleic acid                                                                         ##STR656##  A  a  16  217-229/0.04                                                                          67.52                                                                              67.62                                                                              8.72                                                                               8.90                                                                               3.03                                                                               2.98                812                                                                               Linoleic acid                                                                         ##STR657##  F  d  16  220-239/0.06                                                                          68.06                                                                              68.17                                                                              8.82                                                                               8.93                                                                               2.94                                                                               2.78                813                                                                               Linoleic acid                                                                         ##STR658##  B  b  20  212-223/0.05                                                                          81.55                                                                              81.75                                                                              10.90                                                                              11.08                                                                              3.52                                                                               3.40                814                                                                               Linoleic acid                                                                         ##STR659##  A  e  16  218-222/0.07                                                                          74.69                                                                              74.88                                                                              9.65                                                                               9.76                                                                               3.35                                                                               3.18                815                                                                               Linoleic acid                                                                         ##STR660##  E  a  18  220-218/0.06                                                                          74.69                                                                              74.81                                                                              9.65                                                                               9.82                                                                               3.35                                                                               3.19                816                                                                               Linoleic acid                                                                         ##STR661##  A  a  12  216-218/0.04                                                                          78.40                                                                              78.60                                                                              10.48                                                                              10.59                                                                              3.39                                                                               3.21                817                                                                               Linoleic acid                                                                         ##STR662##  A  a  10  218-229/0.03                                                                          78.40                                                                              78.46                                                                              10.48                                                                              10.53                                                                              3.39                                                                               3.19                818                                                                               Linoleic acid                                                                         ##STR663##  B  b  16  215-226/0.03                                                                          78.40                                                                              78.52                                                                              10.48                                                                              10.62                                                                              3.39                                                                               3.20                819                                                                               Oleic acid                                                                            ##STR664##  A  a  10  205-220/0.07                                                                          81.29                                                                              81.41                                                                              11.45                                                                              11.56                                                                              3.39                                                                               3.29                820                                                                               Oleic acid                                                                            ##STR665##  A  a  10  211-223/0.07                                                                          81.44                                                                              81.62                                                                              11.55                                                                              11.71                                                                              3.28                                                                               3.09                821                                                                               Oleic acid                                                                            ##STR666##  B  b  18  224-238/0.07                                                                          67.24                                                                              67.51                                                                              9.05                                                                               9.11                                                                               3.01                                                                               2.89                822                                                                               Isostearic acid                                                                       ##STR667##  A  c  12  200-215/0.08                                                                          80.73                                                                              80.91                                                                              11.83                                                                              11.94                                                                              3.40                                                                               3.33                823                                                                               Isostearic acid                                                                       ##STR668##  A  d  16  206-224/0.07                                                                          81.33                                                                              81.52                                                                              12.11                                                                              12.42                                                                              3.06                                                                               3.00                824                                                                               Isostearic acid                                                                       ##STR669##  C  e  14  218-239/0.06                                                                          74.02                                                                              74.21                                                                              10.43                                                                              10.56                                                                              3.32                                                                               3.06                825                                                                               Isostearic acid                                                                       ##STR670##  D  d  14  215-226/0.05                                                                          66.95                                                                              67.13                                                                              9.44                                                                               9.57                                                                               3.00                                                                               3.05                826                                                                               Isostearic acid                                                                       ##STR671##  E  a  14  218-230/0.05                                                                          77.64                                                                              77.74                                                                              11.34                                                                              11.43                                                                              3.35                                                                               3.14                827                                                                               Isostearic acid                                                                       ##STR672##  B  b  20  218-224/0.05                                                                          78.14                                                                              78.37                                                                              11.53                                                                              11.68                                                                              3.14                                                                               3.02                828                                                                               Linolenic acid                                                                        ##STR673##  A  e  14  216-230/0.05                                                                          79.61                                                                              79.76                                                                              10.18                                                                              10.35                                                                              3.29                                                                               3.14                829                                                                               Linolenic acid                                                                        ##STR674##  C  e  8   215- 227/0.05                                                                         79.61                                                                              79.75                                                                              10.18                                                                              10.30                                                                              3.29                                                                               3.11                830                                                                               Linolenic acid                                                                        ##STR675##  E  a  16  212-220/0.05                                                                          81.97                                                                              82.18                                                                              10.45                                                                              10.50                                                                              3.54                                                                               3.47                831                                                                               Linolenic acid                                                                        ##STR676##  A  f  10  198-218/0.03                                                                          75.09                                                                              75.21                                                                              9.14                                                                               9.34                                                                               3.36                                                                               3.33                832                                                                               Linseed oil acid                                                                      ##STR677##  F  a  18  203-203/0.03                                   833                                                                               Linseed oil acid                                                                      ##STR678##  B  b  20  200-218/0.03                                   834                                                                               Safflower oil acid                                                                    ##STR679##  A  a  12  203-215/0.03                                   835                                                                               Safflower oil acid                                                                    ##STR680##  A  a  12  209-224/0.05                                   836                                                                               Safflower oil acid                                                                    ##STR681##  A  f  12  208-220/0.05                                   837                                                                               Safflower oil acid                                                                    ##STR682##  F  e  14  220-225/0.03                                   838                                                                               Soybean oil acid                                                                      ##STR683##  A  a  12  210-232/0.05                                   839                                                                               Sunflower oil acid                                                                    ##STR684##  A  a  10  208-232/0.05                                   840                                                                               Castor oil acid                                                                       ##STR685##  A  c  10  205-225/0.05                                   841                                                                               Rape-seed oil acid                                                                    ##STR686##  C  d  12  220-229/0.05                                   842                                                                               Cottonseed oil acid                                                                   ##STR687##  D  e  12  218-233/0.05                                   843                                                                               Olive oil acid                                                                        ##STR688##  E  a  14  204-226/0.05                                   844                                                                               Peanut oil acid                                                                       ##STR689##  A  e  10  218-228/0.05                                   845                                                                               Locust oil acid                                                                       ##STR690##  A  e  10  215-225/0.05                                   846                                                                               Chrysalis oil acid                                                                    ##STR691##  B  b  20  232-241/0.05                                   847                                                                               Shark oil acid                                                                        ##STR692##  A  e  10  225-244/0.05                                   848                                                                               Sardine oil acid                                                                      ##STR693##  F  e  10  206-220/0.06                                   849                                                                               Mackerel oil acid                                                                     ##STR694##  A  a  12  214-231/0.05                                   850                                                                               Herring oil acid                                                                      ##STR695##  C  a  12  194-228/0.05                                   851                                                                               Saurel oil acid                                                                       ##STR696##  A  a  10  197-229/0.07                                   852                                                                               God oil acid                                                                          ##STR697##  F  e  12  198-228/0.05                                   853                                                                               Gray mullet oil acid                                                                  ##STR698##  A  f  8   193-238/0.06                                   854                                                                               Menhaden oil acid                                                                     ##STR699##  A  d  12  188-238/0.05                                   855                                                                               Flatfish oil acid                                                                     ##STR700##  A  c  12  194-237/0.05                                   856                                                                               Residual oil acid                                                                     ##STR701##  A  a  12  200-228/0.05                                   __________________________________________________________________________

EXAMPLE 857

A mixture of 28 g. of linoleic acid, 21 g. of α-benzylbenzylamine, 300 ml. of toluene and 0.4 g. of p-toluenesulfonic acid was refluxed for 8 hrs. using water separator. The toluene layer was washed with acid, alkali and water, and was then dried, concentrated and purified by chromatography on an alumina column whereby 29.2 g. of a semisolid was obtained. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       83.60          83.70                                               H (%)        9.87          10.08                                               N (%)        3.05           3.08                                               ______________________________________                                    

Examples 858-888 are shown in the following table, in which:

Dehydrating agent:

A. p-Toluenesulfonic acid.

B. p-Toluenesulfonic acid chloride.

C. sulfuric acid.

D. phenolsulfonic acid.

E. ira-400.

f. amberlist - 15.

Solvent:

a. Toluene.

b. Pyridine.

c. Benzene.

d. Chloroform.

e. Xylene.

f. Tetrachlorocarbon.

    __________________________________________________________________________                                   Reac-     C %     H %     N %                                                  tion      Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                          Sol-                                                                              time                                                                               Pro-  reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti               Example                                                                             Acid       Amine  Agent                                                                              vent                                                                              (hr)                                                                               perty cal cal cal cal cal cal                __________________________________________________________________________     858  Linoleic acid                                                                              d (+) B   b  20  45°-50°                                                                83.60                                                                              83.77                                                                               9.87                                                                              10.04                                                                              3.05                                                                               3.15                               [α].sub.D +26.6                                          859  Linoleic acid                                                                              l (-) E   e  12  "     83.60                                                                              83.79                                                                               9.87                                                                              10.01                                                                              3.05                                                                               3.14                               [α].sub.D -27.1                                          860  Oleic acid dl (±)                                                                             A   c  10  Semi- 83.24                                                                              83.36                                                                              10.26                                                                              10.32                                                                              3.03                                                                               3.14                                                 solid                                        861  Isostearic acid                                                                           dl (±)                                                                             A   e  10  "     82.88                                                                              83.02                                                                              10.65                                                                              10.41                                                                              3.02                                                                               3.10               862  Isostearic acid                                                                            d (+) C   e  10  "     82.88                                                                              83.05                                                                              10.65                                                                              10.87                                                                              3.02                                                                               3.09               863  Isostearic acid                                                                             l (-)                                                                               A   a  10  "     82.88                                                                              83.06                                                                              10.65                                                                              10.69                                                                              3.02                                                                               3.07               864  Linolenic acid                                                                            dl (±)                                                                             A   a  10  "     83.97                                                                              84.12                                                                               9.47                                                                               9.72                                                                              3.06                                                                               3.12               865  Linseed oil fatty acid                                                                    dl (±)                                                                             A   a  10  "                                            866  Safflower oil fatty acid                                                                   d (+) A   a  10  "                                            867  Safflower oil fatty acid                                                                   l (-) A   a  10  "                                            868  Safflower oil fatty acid                                                                  dl (±)                                                                             F   f  10  "                                            869  Soybean oil acid                                                                          dl (±)                                                                             A   a  12  "                                            870  Sunflower oil acid                                                                        dl (±)                                                                             A   a  12  "                                            871  Castor oil acid                                                                           dl (±)                                                                             A   a  12  "                                            872  Rape-seed oil acid                                                                        dl (±)                                                                             A   a  12  "                                            873  Cottonseed oil acid                                                                       "      D   a  12  "                                            874  Olive oil acid                                                                            "      A   a  12  "                                            875  Peanut oil acid                                                                           "      A   a  12  "                                            876  Locust oil acid                                                                           "      A   a  12  "                                            877  Chrysalis oil acid                                                                        "      A   a  12  "                                            878  Shark oil acid                                                                            "      A   e  12  "                                            879  Sardine oil acid                                                                          "      A   a  12  "                                            880  Mackerel oil acid                                                                         "      A   a  12  "                                            881  Herring oil acid                                                                          "      A   a  12  "                                            882  Saurel oil acid                                                                           "      A   a  12  "                                            883  Cod oil acid                                                                              "      A   a  12  "                                            884  Gray mullet oil acid                                                                      "      A   a  12  "                                            885  Menhaden oil acid                                                                         "      A   a  12  "                                            886  Flatfish oil acid                                                                         "      A   a  12  "                                            887  Residual oil acid                                                                         "      A   a  12  "                                            __________________________________________________________________________

EXAMPLE 888

Linoleic acid (28 g.), 21 g. of α-benzylbenzylamine and 23.2 g. of dicyclohexyl carbodiimide were individually dissolved in 50 ml. of toluene. The solutions were mixed together in one portion, and the mixed solution was allowed to stand at room temperature for 8 hours. After filtering the solution, the filtrate was washed with acid alkali and water, and was dried, concentrated and purified chromatographically to obtain 22.5 g. of a semi-solid, desired product. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       83.60          84.01                                               H (%)        9.87          10.08                                               N (%)        3.05           3.21                                               ______________________________________                                    

Examples 889-918 are shown in the following table:

    __________________________________________________________________________                                           C %     H %     N %                                                            Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                 Ex.             B                     reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                No.                                                                               Acid     Amine                                                                              BNCNB  Solvent                                                                              α.sub.D                                                                      Property                                                                            cal cal cal cal cal cal                  __________________________________________________________________________     889                                                                               Linoleic acid                                                                           d (+)                                                                               ##STR702##                                                                           Ether +26.7                                                                              45°-50°                                                               83.60                                                                              83.80                                                                               9.87                                                                              10.04                                                                              3.05                                                                               3.14                 890                                                                               Linoleic acid                                                                           l (-)                                                                               ##STR703##                                                                           Dioxane                                                                              -26.9                                                                              "    83.60                                                                              83.71                                                                               9.87                                                                               9.99                                                                              3.05                                                                               3.25                 891                                                                               Oleic acid                                                                              dl (±)                                                                           ##STR704##                                                                           Tetrahydro- furan                                                                        Semi- solid                                                                         83.24                                                                              83.50                                                                              10.26                                                                              10.42                                                                              3.05                                                                               3.19                 892                                                                               Isostearic acid                                                                         dl (±)                                                                           ##STR705##                                                                           Ether     "    82.88                                                                              83.01                                                                              10.65                                                                              10.79                                                                              3.02                                                                               3.17                 893                                                                               Isostearic acid                                                                         d (+)                                                                               ##STR706##                                                                           Benzene   "    82.88                                                                              83.05                                                                              10.65                                                                              10.79                                                                              3.02                                                                               3.17                 894                                                                               Isostearic acid                                                                         l (-)                                                                               ##STR707##                                                                           Toluene   "    82.88                                                                              83.12                                                                              10.65                                                                              10.83                                                                              3.02                                                                               3.25                 895                                                                               Linolenic acid                                                                          dl (±)                                                                           ##STR708##                                                                           Toluene   "    83.97                                                                              84.12                                                                               9.47                                                                               9.71                                                                              3.06                                                                               3.16                 896                                                                               Linseed oil                                                                             dl (±)                                                                           ##STR709##                                                                           Benzene   "                                             897                                                                               Safflower oil                                                                           d (+)                                                                               ##STR710##                                                                           Benzene   "                                             898                                                                               Safflower oil                                                                           l (-)                                                                               ##STR711##                                                                           Toluene   "                                             899                                                                               Safflower oil                                                                           dl (±)                                                                           ##STR712##                                                                           Toluene   "                                             900                                                                               Soybean oil acid                                                                             ##STR713##                                                                           Chloroform                                                                               "                                             901                                                                               Sunflower oil acid                                                                           ##STR714##                                                                           Chloroform                                                                               "                                             902                                                                               Castor oil acid                                                                              ##STR715##                                                                           Toluene   "                                             903                                                                               Rape-seed oil acid                                                                           ##STR716##                                                                           Toluene   "                                             904                                                                               Cottonseed oil acid                                                                          ##STR717##                                                                           Toluene   "                                             905                                                                               Olive oil acid                                                                               ##STR718##                                                                           Toluene   "                                             906                                                                               Peanut oil acid                                                                              ##STR719##                                                                           Benzene   "                                             907                                                                               Locust oil acid                                                                              ##STR720##                                                                           Benzene   "                                             908                                                                               Chrysalis oil acid                                                                           ##STR721##                                                                           Tetrachloro carbon                                                                       "                                             909                                                                               Shark oil acid                                                                               ##STR722##                                                                           Pyridine  "                                             910                                                                               Sardine oil acid                                                                             ##STR723##                                                                           Benzene   "                                             911                                                                               Mackerel oil acid                                                                            ##STR724##                                                                           Ether     "                                             912                                                                               Herring oil acid                                                                             ##STR725##                                                                           Ether     "                                             913                                                                               Saurel oil acid                                                                              ##STR726##                                                                           Ether     "                                             914                                                                               Cod oil acid                                                                                 ##STR727##                                                                           Toluene   "                                             915                                                                               Gray mullet oil acid                                                                         ##STR728##                                                                           Toluene   "                                             916                                                                               Menhaden oil acid                                                                            ##STR729##                                                                           Toluene   "                                             917                                                                               Flatfish oil acid                                                                            ##STR730##                                                                           Toluene   "                                             918                                                                               Residual oil acid                                                                            ##STR731##                                                                           Toluene   "                                             __________________________________________________________________________

EXAMPLE 919

A mixture of 10 g. of linoleic acid and 11 g. of α-benzylbenzylamine was heated at 180° C. for 24 hours. The reaction mixture was purified chromatographically to obtain 14.2 g. of a 45°-48° C. desired product. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       83.60          83.76                                               H (%)        9.87          10.02                                               N (%)        3.05           3.30                                               ______________________________________                                    

Examples 920-942 are shown in the following tables:

    __________________________________________________________________________                          Reac-                                                                          tion Reac-                                                                     temper-                                                                             tion      C %      H %      N %                      Example              ature                                                                               time                                                                               Pro-  Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-              No.  Acid moiety                                                                           Amine                                                                               Agent                                                                              ° C.                                                                         (hr)                                                                               perty tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical               __________________________________________________________________________     920  Linoleic acid                                                                         d (+)    140  36  45°-50°                                                                83.60                                                                               83.72                                                                               9.87                                                                                9.98                                                                              3.05 3.21                921  Linoleic acid                                                                         l (-)    140  36  "     83.60                                                                               83.69                                                                               9.87                                                                                9.98                                                                              3.05 3.22                922  Oleic acid                                                                            dl (±)                                                                               140  40  "     83.24                                                                               83.34                                                                              10.26                                                                               10.41                                                                              3.03 3.06                923  Isostearic acid                                                                       dl (±)                                                                               150  40  "     82.88                                                                               83.05                                                                              10.65                                                                               10.77                                                                              3.02 3.05                924  Isostearic acid                                                                       d (+)    150  40  "     82.88                                                                               83.06                                                                              10.65                                                                               10.71                                                                              3.02 3.13                925  Isostearic acid                                                                       l (-)    180  36  "     82.88                                                                               83.00                                                                              10.65                                                                               10.82                                                                              3.02 3.09                926  Linolenic acid                                                                        dl (±)                                                                               150  40  "     83.97                                                                               84.12                                                                               9.47                                                                                9.63                                                                              3.06 2.99                927  Linseed oil                                                                           dl (±)                                                                               150  40  "                                                928  Safflower oil                                                                         d (+)    180  40  "                                                929  Safflower oil                                                                         l (-)    180  36  "                                                930  Safflower oil                                                                         dl (±)                                                                           Boric                                                                              180  16  "                                                                 acid                                                          __________________________________________________________________________

    __________________________________________________________________________                        Reaction                                                                              Reaction                                             Example            temper-                                                                               time                                                 No.  Acid moiety                                                                              Agent                                                                              ature ° C.                                                                     (hr.)                                                                               Property                                        __________________________________________________________________________     931  Soybean oil acid                                                                             140    40   Semi-                                                                          solid                                           932  Sunflower oil acid                                                                           150    40   "                                               933  Castor oil acid                                                                          Boric                                                                              150    20   "                                                              acid                                                            934  Rape-seed oil acid                                                                           150    40   "                                               935  Cottonseed oil                                                                               160    40   "                                                    acid                                                                      936  Olive oil acid                                                                               150    40   "                                               937  Peanut oil acid                                                                              150    40   "                                               938  Chrysalis oil acid                                                                           150    40   "                                               939  Shark oil acid                                                                               150    40   "                                               940  Sardine oil acid                                                                             150    40   "                                               941  Mackerel oil acid                                                                            150    40   "                                               942  Herring oil acid                                                                             150    40   "                                               __________________________________________________________________________

EXAMPLE 943

A mixture of 10 g. of methyl linoleate and 11.2 g. of α-benzyl-benzylamine was heated in a nitrogen atmosphere at 180° C. for 50 hours removing methanol out of the reaction system. The reaction mixture was purified chromatographically to obtain 15.3 g. desired product up 46°-49° C. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       83.60          83.61                                               H (%)        9.87          10.09                                               N (%)        3.05           3.25                                               ______________________________________                                    

EXAMPLE 944

A mixture of 10 g. of methyl isostearate, 11.2 g. of α-benzyl-benzylamine and 1 g. of sodium methylate. The mixture was reacted at 150° C. for 3 hours, removing methanol during the reaction. Subsequently, the reaction product was dissolved in ether and the ether solution was washed with acid, alkali and water according to ordinary procedures and was then dried and purified chromatographically to obtain 15.8 g. of a semi-solid desired compound. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       82.88          83.78                                               H (%)       10.65          10.21                                               N (%)        3.02           3.16                                               ______________________________________                                    

EXAMPLE 945

A mixture of 10 g. of ethyl oleate, 11 g. of α-benzyl-benzylamine 0.5 g. of sodium and 8 ml. of ethyl alcohol was heated at 160° C. for about 2 hours removing ethyl alcohol. Thereafter, the same treatments as in Example 857 were effected to obtain 14.0 g. of a desired product. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       83.24          83.66                                               H (%)       10.26           9.91                                               N (%)        3.03           3.21                                               ______________________________________                                    

EXAMPLE 946

A mixture of 10 g. of safflower oil and 11 g. of α-benzyl-benzylamine was heated in an autoclave at 200° C. for 22 hours. Immediately thereafter, the same treatments as in Example 857 were effected to obtain 15.0 g. of a desired product.

Examples 947-987 are shown in the following tables:

    __________________________________________________________________________                          Reac-                                                                          tion Reac-   C %     H %     N %                                               temper-                                                                             tion    The-                                                                               An- The-                                                                               An- The-                                                                               An-                      Example              ature                                                                               time                                                                               Pro-                                                                               ore-                                                                               aly-                                                                               ore-                                                                               aly-                                                                               ore-                                                                               aly                      No.  Acid moiety                                                                           Amine                                                                              Agent                                                                               ° C.                                                                         (hr)                                                                               perty                                                                              tical                                                                              tical                                                                              tical                                                                              tical                                                                              tical                                                                              tical                    __________________________________________________________________________     947  Methyl d (+)    160  49  45°-50°                                                              83.60                                                                              83.72                                                                               9.87                                                                              10.11                                                                              3.05                                                                               2.94                          linoleate                                                                 948  Methyl l (-)    160  48  "   83.60                                                                              83.74                                                                               9.87                                                                              10.06                                                                              3.05                                                                               2.87                          linoleate                                                                 949  Ethyl oleate                                                                          d (+)    140  48  Semi-                                                                              83.24                                                                              83.34                                                                              10.26                                                                              10.41                                                                              3.03                                                                               2.90                                                   solid                                            950  Methyl dl (±)                                                                          NaOCH.sub.3                                                                         140   4  "   82.88                                                                              83.10                                                                              10.65                                                                              10.88                                                                              3.02                                                                               2.88                          isostearate                                                               951  Methyl d (+)    140  49  "   82.88                                                                              83.09                                                                              10.65                                                                              10.82                                                                              3.02                                                                               2.91                          isostearate                                                               952  Methyl l (-)    160  56  "   82.88                                                                              83.11                                                                              10.65                                                                              10.72                                                                              3.02                                                                               2.84                          isostearate                                                               953  Methyl d (+)    180  50  "   83.97                                                                              84.21                                                                               9.47                                                                               9.63                                                                              3.06                                                                               2.87                          linolenate                                                                954  Linseed oil                                                                           dl (±)                                                                               180  50  "                                                955  Safflower                                                                             d (+)    180  50  "                                                     oil                                                                       956  Safflower                                                                             l (-)    170  50  "                                                     oil                                                                       957  Safflower                                                                             d (+)    170  60  "                                                     oil methyl                                                                     ester                                                                     __________________________________________________________________________                                         Reaction                                   Example                             tempera- Reaction                          No.      Acid moiety        Agent   ture. ° C.                                                                       time (hr)                                                                             Property                   __________________________________________________________________________     958     Soybean oil acid methyl ester                                                                      Boric acid                                                                             160      50     Semi-solid                 959     Castor oil acid methyl ester                                                                               160      50     "                          960     Cottonseed oil acid methyl ester                                                                           160      50     "                          961     Olive oil acid methyl ester 160      50     "                          962     Peanut oil acid methyl ester                                                                               140      50     "                          963     Shark oil acid methyl ester 180      66     "                          964     Sardine oil acid methyl ester                                                                              180      66     "                          965     Mackerel oil acid methyl ester                                                                             180      56     "                          966     Herring oil acid methyl ester                                                                              180      66     "                          967     Cod oil acid methyl ester   200      65     "                          968     Flatfish acid methyl ester  140      80     "                          969     Soybean oil                 140      60     "                          970     Sunflower oil               140      60     "                          971     Castor oil                  160      60     "                          972     Rape-seed oil               160      60     "                          973     Cottonseed oil              180      60     "                          974     Olive oil                   160      60     "                          975     Peanut oil                  160      60     "                          976     Locust oil                  160      60     "                          977     Chrysalic oil               160      60     "                          978     Shark oil                   160      60     "                          979     Sardine oil                 160      60     "                          980     Mackerel oil                160      60     "                          981     Herring oil         Boric acid                                                                             160      60     "                          982     Saurel oil                  140      60     "                          983     Cod oil                     140      60     "                          984     Gray mullet oil             140      50     "                          985     Menhaden oil                140      50     "                          986     Flatfish oil                140      40     "                          987     Residual oil                140      50     "                          __________________________________________________________________________

EXAMPLE 988

A solution of 30 g. of linoleic acid chloride in 50 ml. of anhydrous ether was added to a solution of 22.5 g. of α-benzyl-benzylamine and 8 g. of trimethylamine in 100 ml. of anhydrous ether. The reaction mixture was boiled for 2 hours after addition. Subsequently, the ether solution was washed with acid, alkali and water, and was dried, concentrated and purified chromatographically in the same manner as in Example 857 to obtain 48 g. of a desired product. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       83.60          83.79                                               H (%)        9.87          10.04                                               N (%)        3.05           3.27                                               ______________________________________                                    

Examples 989-1019 are shown in the following tables:

    __________________________________________________________________________                                            C %     H %     N %                                                            Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                Example                                reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti-               No.  Acid  Amine                                                                              Agent Solvent α.sub.0                                                                       Property                                                                            cal cal cal cal cal cal                 __________________________________________________________________________     989  Linoleic                                                                             dl (±)                                                                          Triethyl-                                                                            Ether [α].sub.D                                                                  +27.0                                                                               47-50°                                                                       83.60                                                                              83.88                                                                               9.87                                                                               9.99                                                                              3.05                                                                               3.12                     acid Cl   amine                                                           990  Linoleic                                                                       acid Cl                                                                              d (+)                                                                              NaOH  Acetone [α].sub.D                                                                +27.0                                                                               "    83.60                                                                              83.79                                                                               9.87                                                                               9.91                                                                              3.05                                                                               2.88                991  Linoleic                                                                       acid Cl                                                                              l (-)                                                                              Pyridine                                                                             Toluene [α].sub.D                                                                -27.5                                                                               "    83.60                                                                              83.71                                                                               9.87                                                                              10.21                                                                              3.05                                                                               2.79                992  Oleic acid                                                                           dl (±)                                                                          Pyridine                                                                             Benzene      Semi-                                                                               83.24                                                                              83.51                                                                              10.26                                                                              10.34                                                                              3.03                                                                               3.00                     Cl                           solid                                        993  Isostearic                                                                           dl (±)                                                                          K.sub.2 CO.sub.3                                                                     M I B K      "    82.88                                                                              83.09                                                                              10.65                                                                              10.91                                                                              3.02                                                                               2.81                     acid Cl                                                                   994  Isostearic      Acetone-                                                       acid Cl                                                                              d (+)                                                                              NaOH  water        "    82.88                                                                              83.09                                                                              10.65                                                                              10.90                                                                              3.02                                                                               2.79                995  Isotearic       Dioxane-                                                       acid Cl                                                                              l (-)                                                                              KOH   water        "    82.88                                                                              83.01                                                                              10.65                                                                              10.87                                                                              3.02                                                                               2.99                996  Linolenic                                                                            dl (±)                                                                          Dimethyl-                                                                            Ether        "    83.97                                                                              84.12                                                                               9.47                                                                               9.67                                                                              3.06                                                                               2.95                     acid Cl   aniline                                                         997  Linseed                                                                              dl (±)                                                                          Triethyl-                                                                            Toluene      "                                                 oil Cl    amine                                                           998  Safflower                                                                            d (+)                                                                              Triethyl-                                                                            Toluene      "                                                 oil Cl    amine                                                           999  Safflower                                                                            l (-)                                                                              Triethyl-                                                                            Toluene      "                                                 oil Cl    amine                                                           1000 Safflower Triethyl-                                                                            Toluene      "                                                 oil Cl                                                                               dl (±)                                                                          amine                                                           __________________________________________________________________________     Example                                                                        No.        Acid                Agent        Solvent      Property              __________________________________________________________________________     1001      Soybean oil acid                                                                            Cl     Pyridine      Toluene      Semi-solid            1002      Sunflower oil acid                                                                          Cl     K.sub.2 CO.sub.3                                                                             M I B K      "                     1003      Castor oil acid                                                                             Cl     Dimethylaniline                                                                              Toluene      "                     1004      Rape seed oil acid                                                                          Cl     Trimethylamine                                                                               Ether        "                     1005      Cottonseed oil acid                                                                         Cl     Pyridine      Ether        "                     1006      Olive oil acid                                                                              Cl     K.sub.2 CO.sub.3                                                                             Acetone-     "                                                                 water                              1007      Peanut oil acid                                                                             Cl     NaOH          Tetrahydro-  "                                                                 furan-water                        1008      Locust oil acid                                                                             Cl     KOH           Dioxane-     "                                                                 water                              1009      Chrysalis oil acid                                                                          Cl     K.sub.2 CO.sub.3                                                                             M I B K      "                     1010      Shark oil acid                                                                              Cl     Na.sub.2 CO.sub.3                                                                            Acetone      "                     1011      Sardine oil acid                                                                            Cl     Triethylamine Toluene      "                     1012      Mackerel oil acid                                                                           Cl     Triethylamine Toluene      "                     1013      Herring oil acid                                                                            Cl     Triethylamine Ether        "                     1014      Saurel oil acid                                                                             Cl     Triethylamine Ether        "                     1015      Cod oil acid Cl     Triethylamine Ether        "                     1016      Gray mullet oil acid                                                                        Cl     NaOH          Acetone-water                                                                               "                     1017      Menhaden oil acid                                                                           Cl     Pyridine      Ether        "                     1018      Flatfish oil acid                                                                           Cl     Pyridine      Toluene      "                     1019      Residual oil acid                                                                           Cl     Pyridine      Ether        "                     __________________________________________________________________________

EXAMPLE 1020

A solution of 20 g. of linoleic acid, 17 g. of α-methyl-p-nitrobenzylamine 0.5 g. of p-toluenesulfonic acid in 300 ml. of toluene was refluxed using a water-separator for 8 hours. The toluene layer was washed with acid, alkali and water, and was then dried and concentrated to obtain 22.3 g. of a desired product, n_(D) ²³ 1.5111. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       72.86          72.67                                               H (%)        9.41           9.21                                               N (%)        6.54           6.66                                               ______________________________________                                    

Examples 1021-1051 are shown in the following tables, in which:

Dehydration assistant:

A. p-Toluenesulfonic acid.

B. p-Toluenesulfonic acid chloride.

C. sulfuric acid.

D. phenolsulfonic acid.

E. ira-400.

f. amberlist-15.

Solvent:

a. Toluene.

b. Pyridine.

c. Benzene.

d. Chloroform.

e. Xylene.

f. Tetrachlorocarbon.

    __________________________________________________________________________                                   Reac-   C %     H %     N %                                                    tion    Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                 Ex.                        Solv-                                                                             time    reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                No.                                                                               Acid   Amine        Agent                                                                              ent                                                                               (hr)                                                                               n.sub.D                                                                            cal cal cal cal cal cal                  __________________________________________________________________________     1021                                                                              Oleic acid                                                                             ##STR732##  A   a   8  23° C 1.5123                                                                72.93                                                                              73.16                                                                               9.97                                                                              10.13                                                                              6.30                                                                               6.05                 1022                                                                              Linolenic acid                                                                         ##STR733##  B   b  20  23°  C 1.5100                                                               73.60                                                                              73.90                                                                               9.15                                                                               9.32                                                                              6.36                                                                               6.12                 1023                                                                              Linoleic acid                                                                          ##STR734##  A   e  10  22.5° C 1.5133                                                              73.26                                                                              73.52                                                                               9.56                                                                               9.72                                                                              6.33                                                                               6.14                 1024                                                                              Linoleic acid                                                                          ##STR735##  D   c  10  26° C 1.5109                                                                72.86                                                                              72.99                                                                               9.41                                                                               9.58                                                                              6.54                                                                               6.37                 1025                                                                              Isostearic acid                                                                        ##STR736##  C   a  14  28° C 1.5155                                                                72.18                                                                              72.32                                                                              10.25                                                                              10.50                                                                              6.48                                                                               6.21                 1026                                                                              Isostearic acid                                                                        ##STR737##  E   e  12  28° C 1.3152                                                                72.18                                                                              72.22                                                                              10.25                                                                              10.45                                                                              6.48                                                                               6.11                 1027                                                                              Safflower oil acid                                                                     ##STR738##  F   f  12  23° C 1.5138                          1028                                                                              Soybean oil acid                                                                       ##STR739##  A   e  12  20°  C 1.5131                         1029                                                                              Sesame oil acid                                                                        ##STR740##  A   e  12  19°  C 1.5114                         1030                                                                              Castor oil acid                                                                        ##STR741##  C   a  12  22°  C 1.5122                         1031                                                                              Corn oil acid                                                                          ##STR742##  A   a  12  20°  C 1.5133                         __________________________________________________________________________

    __________________________________________________________________________     Example                           Reaction                                     No.  Acid      Amine      Agent                                                                              Solvent                                                                            time n.sub.D                                 __________________________________________________________________________     1032 Cottonseed oil acid                                                                       ##STR743##                                                                               A   a   12   23° C                                                                       1.5129                              1033 Olive oil acid                                                                            ##STR744##                                                                               D   a    8   25° C                                                                       1.5139                              1034 Linssed oil acid                                                                          ##STR745##                                                                               A   d   12   28.5° C                                                                     1.5119                              1035 Rape-seed oil acid                                                                        ##STR746##                                                                               A   f   10   145 1.5139                              1036 Rice bran oil acid                                                                        ##STR747##                                                                               A   a   10   18° C                                                                       1.5123                              1037 Chrysalis oil acid                                                                        ##STR748##                                                                               D   a   10   23° C                                                                       1.5100                              1038 Flatfish oil acid                                                                         ##STR749##                                                                               C   a   12   22° C                                                                       1.5123                              1039 Shark oil acid                                                                            ##STR750##                                                                               E   e   12   22° C                                                                       1.5144                              1040 Whale oil acid                                                                            ##STR751##                                                                               A   d   12   23° C                                                                       1.5134                              1041 Cuttlefish oil acid                                                                       ##STR752##                                                                               B   b   20   24.5° C                                                                     1.5127                              1042 Sardine oil acid                                                                          ##STR753##                                                                               F   e   12   23° C                                                                       1.5221                              1043 Mackerel oil acid                                                                         ##STR754##                                                                               B   b   20   22.5° C                                                                     1.5147                              1044 Saury pike oil acid                                                                       ##STR755##                                                                               A   d   14   26.5° C                                                                     1.5237                              1045 Herring oil acid                                                                          ##STR756##                                                                               A   a   10   30° C                                                                       1.5114                              1046 Saurel oil acid                                                                           ##STR757##                                                                               C   e   14   30° C                                                                       1.5138                              1047 Menhaden oil acid                                                                         ##STR758##                                                                               D   a   12   32° C                                                                       1.5149                              1048 Cod oil acid                                                                              ##STR759##                                                                               E   f   12   30.5° C                                                                     1.5139                              1049 Liver oil acid                                                                            ##STR760##                                                                               F   e   12   24.5° C                                                                     1.5210                              1050 Menuke oil acid                                                                           ##STR761##                                                                               A   a   12   21.5° C                                                                     1.5140                              1051 Residual oil acid                                                                         ##STR762##                                                                               A   a   12   20.3° C                                                                     1.5133                              __________________________________________________________________________

EXAMPLE 1052

Linoleic acid (20 g.), 17 g. of α-methyl-o-nitrobenzylamine and 20 g. of dicyclohexyl carbodiimdie were individually dissolved in 100 ml. of toluene. The solutions were mixed together at one portion, and the mixed solution was allowed to stand at room temperature for 8 hours. After filtering the solution, the filtrate was washed with acid, alkali and water, and was then dried, concentrated and distilled to obtain 11.1 g. of a desired product, n_(D) ²³ 1.5140. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       72.86          72.68                                               H (%)        9.41           9.03                                               N (%)        6.54           7.01                                               ______________________________________                                    

Examples 1053-1073 are shown in the following table:

    __________________________________________________________________________                                             C %     H %     N %                                       Agent                Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-               Ex.                BNCNB         °C                                                                             reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti-              No.                                                                               Acid Amine      B        Solvent                                                                             n.sub.D                                                                               cal cal cal cal cal cal                __________________________________________________________________________     1053                                                                              Oleic acid                                                                           ##STR763##                                                                                ##STR764##                                                                             Ether                                                                               25°C                                                                       1.5120                                                                             72.93                                                                              73.22                                                                              9.97                                                                               10.12                                                                              6.30                                                                               6.05               1054                                                                              Linolenic acid                                                                       ##STR765##                                                                                ##STR766##                                                                             Toluene                                                                             23°C                                                                       1.5106                                                                             73.60                                                                              73.88                                                                              9.15                                                                               9.43                                                                               6.36                                                                               6.12               1055                                                                              Linoleic acid                                                                        ##STR767##                                                                                ##STR768##                                                                             Benzene                                                                             22° C                                                                      1.5155                                                                             73.26                                                                              73.61                                                                              9.56                                                                               9.72                                                                               6.33                                                                               6.28               1056                                                                              Linoleic acid                                                                        ##STR769##                                                                                ##STR770##                                                                             Benzene                                                                             28°C                                                                       1.5106                                                                             72.86                                                                              73.05                                                                              9.41                                                                               9.66                                                                               6.54                                                                               6.39               1057                                                                              Isostearic acid                                                                      ##STR771##                                                                                ##STR772##                                                                             Cyclo-  hexane                                                                      29°C                                                                       1.5153                                                                             72.18                                                                              72.32                                                                              10.25                                                                              10.48                                                                              6.48                                                                               6.39               1058                                                                              Isostearic acid                                                                      ##STR773##                                                                                ##STR774##                                                                             Benzene                                                                             28°C                                                                       1.5153                                                                             72.18                                                                              72.38                                                                              10.25                                                                              10.47                                                                              6.48                                                                               6.36               1059                                                                              Safflower oil acid                                                                   ##STR775##                                                                                ##STR776##                                                                             Chloro- form                                                                        24°C                                                                       1.5137                                     1060                                                                              Soybean oil acid                                                                     ##STR777##                                                                                ##STR778##                                                                             Tetra- chloro- carbon                                                               24°C                                                                       1.5131                                     1061                                                                              Sesame oil acid                                                                      ##STR779##                                                                                ##STR780##                                                                             Benzene                                                                             22°C                                                                       1.5115                                     1062                                                                              Castor oil acid                                                                      ##STR781##                                                                                ##STR782##                                                                             Ether                                                                               22°C                                                                       1.5122                                     1063                                                                              Corn oil acid                                                                        ##STR783##                                                                                ##STR784##                                                                             Benzene                                                                             20°C                                                                       1.5132                                     1064                                                                              Cotton- seed oil acid                                                                ##STR785##                                                                                ##STR786##                                                                             Benzene                                                                             24°C                                                                       1.5127                                     1065                                                                              Olive oil acid                                                                       ##STR787##                                                                                ##STR788##                                                                             Benzene                                                                             22°C                                                                       1.5142                                     1066                                                                              Linseed oil acid                                                                     ##STR789##                                                                                ##STR790##                                                                             Toluene                                                                             24°C                                                                       1.5122                                     1067                                                                              Flatfish oil acid                                                                    ##STR791##                                                                                ##STR792##                                                                             Pyridine                                                                            22°C                                                                       1.5124                                     1068                                                                              Whale oil acid                                                                       ##STR793##                                                                                ##STR794##                                                                             Dioxane                                                                             23°C                                                                       1.5133                                     1069                                                                              Cuttlefish oil acid                                                                  ##STR795##                                                                                ##STR796##                                                                             Tetra- hydro- furan                                                                 25°C                                                                       1.5130                                     1070                                                                              Sardine oil acid                                                                     ##STR797##                                                                                ##STR798##                                                                             Pyridine                                                                            24°C                                                                       1.5145                                     1071                                                                              Saurel oil acid                                                                      ##STR799##                                                                                ##STR800##                                                                             Benzene                                                                             24°C                                                                       1.5141                                     1072                                                                              Liver oil acid                                                                       ##STR801##                                                                                ##STR802##                                                                             Ether                                                                               22°C                                                                       1.5214                                     1073                                                                              Residual oil acid                                                                    ##STR803##                                                                                ##STR804##                                                                             Toluene                                                                             20°C                                                                       1.5136                                     __________________________________________________________________________

EXAMPLE 1074

A mixture of 10 g. of linoleic acid and 9 g. of α-methyl-m-nitrobenzylamine was heated at 180° C. for 24 hours removing water during the reaction. The reaction product was dissolved in ether, and the ether solution was washed with acid, alkali and water and was then dried and concentrated to obtain 11.1 g. of a desired product, n_(D) ²⁸ 1.5138. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       72.86          72.68                                               H (%)        9.41           9.24                                               N (%)        6.54           6.86                                               ______________________________________                                    

Examples 1075-1105 are shown in the following table:

    __________________________________________________________________________                              Reac-                                                                          tiom                                                                               Reac-      C%      H%      N%                                              tempe-                                                                             tion       Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-               Ex.                      rature                                                                             time       reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti-              No.                                                                               Acid Amine        Agent                                                                              °C.                                                                         (hr)                                                                               n.sub.D                                                                               cal cal cal cal cal cal                __________________________________________________________________________     1075                                                                              Oleic acid                                                                           ##STR805##      180 24  22° C 1.5122                                                                   72.93                                                                              73.20                                                                               9.97                                                                              10.17                                                                              6.30                                                                               6.12               1076                                                                              Linolenic acid                                                                       ##STR806##      180 24  24 " 1.5004                                                                           73.60                                                                              73.81                                                                               9.15                                                                               9.32                                                                              6.36                                                                               6.16               1077                                                                              Linoleic acid                                                                        ##STR807##      180 24  25 " 1.5155                                                                           73.26                                                                              73.55                                                                               9.56                                                                               9.70                                                                              6.33                                                                               6.17               1078                                                                              Linoleic acid                                                                        ##STR808##  Boric acid 5%                                                                      160 12  23 " 1.5111                                                                           72.86                                                                              73.06                                                                               9.41                                                                               9.68                                                                              6.54                                                                               6.31               1079                                                                              Isostearic acid                                                                      ##STR809##      160 37  23.5" 1.5158                                                                          72.18                                                                              72.40                                                                              10.25                                                                              10.33                                                                              6.48                                                                               6.40               1080                                                                              Isostearic acid                                                                      ##STR810##      145 39  24.5" 1.5156                                                                          72.18                                                                              72.39                                                                              10.25                                                                              10.46                                                                              6.48                                                                               6.41               1081                                                                              Safflower oil acid                                                                   ##STR811##      160 36  24° C 1.5137                           1082                                                                              Soybean oil acid                                                                     ##STR812##      180 28  26 " 1.5124                                   1083                                                                              Sesame oil acid                                                                      ##STR813##      180 24  26 " 1.5104                                   1084                                                                              Castor oil acid                                                                      ##STR814##      170 24  25.5" 1.5119                                  1085                                                                              Corn oil acid                                                                        ##STR815##      165 34  23.5" 1.5114                                  1086                                                                              Cotton- seed oil acid                                                                ##STR816##      160 34  24.5" 1.5128                                  1087                                                                              Olive oil acid                                                                       ##STR817##      160 36  23.5" 1.5129                                  1088                                                                              Linseed oil acid                                                                     ##STR818##      160 34  22.5" 1.5120                                  1089                                                                              Rapeseed oil acid                                                                    ##STR819##  Boric acid 5%                                                                      160 10  23 " 1.5140                                   1090                                                                              Rice bran oil acid                                                                   ##STR820##      160 32  23 " 1.5122                                   1091                                                                              Chrysalis oil acid                                                                   ##STR821##      160 32  23 " 1.5110                                   1092                                                                              Flatfish oil acid                                                                    ##STR822##      160 32  21 " 1.5122                                   1093                                                                              Sark oil acid                                                                        ##STR823##      160 32  22 " 1.5140                                   1094                                                                              Whale oil acid                                                                       ##STR824##      160 37  21 " 1.5131                                   1095                                                                              Cuttlefish oil acid                                                                  ##STR825##      160 32  23.5" 1.5130                                  1096                                                                              Sardine oil acid                                                                     ##STR826##      160 32  21.5" 1.5222                                  1097                                                                              Mackerel oil acid                                                                    ##STR827##      145 37  18.5" 1.5152                                  1098                                                                              Saurypike oil acid                                                                   ##STR828##      145 34  19 " 1.5157                                   1099                                                                              Herring oil acid                                                                     ##STR829##      145 34  20 " 1.5120                                   1100                                                                              Saurel oil acid                                                                      ##STR830##      160 34  20.5" 1.5150                                  1101                                                                              Men- haden oil acid                                                                  ##STR831##      145 35  22.5" 1.5160                                  1102                                                                              Cod oil acid                                                                         ##STR832##      145 37  20 " 1.5150                                   1103                                                                              Liver oil acid                                                                       ##STR833##      160 37  20 " 1.5210                                   1104                                                                              Menuke oil acid                                                                      ##STR834##      160 37  19 " 1.5133                                   1105                                                                              Residual oil acid                                                                    ##STR835##  Boric acid 10%                                                                     160 10  18.5" 1.5142                                  __________________________________________________________________________

EXAMPLE 1106

A mixture of 10 g. of methyl linoleate and 10 g. of α-methyl-p-nitrobenzylamine was heated in a nitrogen atmosphere at 180° C. for 30 hours removing methanol. The same treatments as in Example 857 were effected to obtain 12.8 g. of a desired product, n_(D) ²⁸ 1.5106. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       72.86          73.06                                               H (%)        9.41           9.62                                               N (%)        6.54           6.30                                               ______________________________________                                    

EXAMPLE 1107

A mixture of 10 g. of methyl isostearate, 10 g. of α-methyl-p-nitrobenzylamine and 1 g. of sodium methylate was heated at 150° for 3 hours removing methanol. The reaction product was washed with acid, alkali and water according to ordinary procedures and was then dried to obtain 12.3 g. of a desired product, n_(D) ²⁸ 1.5063. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       72.18          72.24                                               H (%)       10.25          10.28                                               N (%)        6.48           6.52                                               ______________________________________                                    

EXAMPLE 1108

To a mixture of 10 g. of ethyl oleate and 9 g. of α-methyl-p-nitrobenzylamine was added a solution of 0.5 g. of sodium in 8 ml. of ethyl alcohol. The mixture was heated at 160° for about 2 hours removing ethyl alcohol. Thereafter, the same treatments as in Example 857 were effected to obtain12.8 g. of a desired product, n_(D) ²² 1.5150. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       72.52          72.77                                               H (%)        9.83           9.99                                               N (%)        6.51           6.30                                               ______________________________________                                    

EXAMPLE 1109

A mixture of 10 g. of safflower oil and 10 g. of α-methyl-p-nitrobenzylamine was heated in an autoclave at 200° C. for 12 hours, and 13.0 g. of a desired product, n_(D) ²⁸ 1.5140 was obtained.

Examples 1110-1164 are shown in the following table:

    __________________________________________________________________________                             Reac-                                                                          tion Reac-       C %     H %     N %                                           tempera-                                                                            tion        Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                               Theo-                                                                             Ana-               Ex.                                                                               RCOA (A)             ture time        reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                             lyti               No.                                                                               Acid Amine      Agent                                                                               ° C.                                                                         (hr)                                                                                .sup.n D                                                                              cal cal cal cal cal                                                                               cal                __________________________________________________________________________     1110                                                                              Oleic acid (OCH.sub.3)                                                               ##STR836##                                                                               t-C.sub.4 H.sub.9 OK                                                                180  4   22° C 1.5122                                                                    72.93                                                                              73.21                                                                              9.97                                                                               10.05                                                                              6.30                                                                              6.11               1111                                                                              Linolenic acid (OCH.sub.3)                                                           ##STR837##     160  37  22° C 1.5000                                                                    73.60                                                                              73.88                                                                              9.15                                                                               9.41                                                                               6.36                                                                              6.24               1112                                                                              Linoleic acid (OCH.sub.3)                                                            ##STR838##     160  37  23.5° C 1.5157                                                                  73.26                                                                              73.61                                                                              9.56                                                                               9.76                                                                               6.33                                                                              6.19               1113                                                                              Linoleic acid (OCH.sub.3)                                                            ##STR839##                                                                               Boric- acid 5 %                                                                     160  12  22° C 1.5114                                                                    72.86                                                                              73.04                                                                              9.41                                                                               9.60                                                                               6.54                                                                              6.47               1114                                                                              Isostearic acid (OCH.sub.3)                                                          ##STR840##     160  40  24° C 1.5149                                                                    72.18                                                                              72.33                                                                              10.25                                                                              10.50                                                                              6.48                                                                              6.43               1115                                                                              Isostearic acid (OCH.sub.3)                                                          ##STR841##     160  40  24° C 1.5156                                                                    72.18                                                                              72.41                                                                              10.25                                                                              10.54                                                                              6.48                                                                              6.41               1116                                                                              Safflower oil acid (OCH.sub.3)                                                       ##STR842##                                                                               160  40   24° C 1.5135                               1117                                                                              Soybean oil acid (OCH.sub.3)                                                         ##STR843##                                                                               180  40   24° C 1.5122                               1118                                                                              Sesame oil acid (OC.sub.2 H.sub.5)                                                   ##STR844##                                                                               170  35   24° C 1.5096                               1119                                                                              Castor oil acid (OCH.sub.3)                                                          ##STR845##                                                                               180  35   24° C 1.5120                               1120                                                                              Corn oil acid (OCH.sub.3)                                                            ##STR846##                                                                               180  35   25.5° C 1.5116                             1121                                                                              Cotton- seed oil acid (OCH.sub.3)                                                    ##STR847##                                                                               180  35   26° C 1.5126                               1122                                                                              Olive oil acid (OCH.sub.3)                                                           ##STR848##                                                                               180  35   26° C 1.5122                               1123                                                                              Linseed oil acid (OC.sub.2 H.sub.5)                                                  ##STR849##     160  42  24° C 1.5120                           1124                                                                              Rapeseed oil acid (OCH.sub.3)                                                        ##STR850##     160  42  24° C 1.5134                           1125                                                                              Rice bran oil acid (OCH.sub.3)                                                       ##STR851##     160  42  24° C 1.5120                           1126                                                                              Chrysalis oil acid (OCH.sub.3)                                                       ##STR852##     160  42  24.5° C 1.5116                         1127                                                                              Flatfish oil acid (OCH.sub.3)                                                        ##STR853##     160  40  22° C 1.5123                           1128                                                                              Shark oil acid (OCH.sub.3)                                                           ##STR854##     160  37  23° C 1.5142                           1129                                                                              Whale oil acid (OCH.sub.3)                                                           ##STR855##     160  37  23° C 1.5132                           1130                                                                              Cuttlefish oil acid (OCH.sub.3)                                                      ##STR856##     160  37  23° C 1.5129                           1131                                                                              Sardine oil acid (OCH.sub.3)                                                         ##STR857##     160  40  25° C 1.5220                           1132                                                                              Maclerel oil acid (OCH.sub.3)                                                        ##STR858##     160  40  23.5° C 1.5144                         1133                                                                              Saury pike oil acid (OCH.sub.3)                                                      ##STR859##     160  40  23° C 1.5147                           1134                                                                              Herring oil acid (OCH.sub.3)                                                         ##STR860##     160  40  23° C 1.5120                           1135                                                                              Saurel oil acid (OCH.sub.3)                                                          ##STR861##                                                                               Boric- acid                                                                         160  12  23° C 1.5146                           1136                                                                              Menha- den oil acid (OCH.sub.3)                                                      ##STR862##     160  40  23° C 1.5157                           1137                                                                              Cod oilacid (OCH.sub.3)                                                              ##STR863##     160  40  22.5° C 1.5141                         1138                                                                              Liver oil acid (OCH.sub.3)                                                           ##STR864##     160  40  23° C 1.5218                           1139                                                                              Menuke oil acid (OCH.sub.3)                                                          ##STR865##     160  40  24° C 1.5129                           1140                                                                              Residual oil acid (OCH.sub.3)                                                        ##STR866##     160  40  25° C 1.5133                           1141                                                                              Soybean oil                                                                          ##STR867##     160  42  23° C 1.5129                           1142                                                                              Sesame oil                                                                           ##STR868##     160  40  23° C 1.5109                           1143                                                                              Castor oil                                                                           ##STR869##                                                                               Boric- acid 5 %                                                                     170  40  24° C 1.5122                           1144                                                                              Corn oil                                                                             ##STR870##     180  30  23° C 1.5120                           1145                                                                              Cotton- seed oil                                                                     ##STR871##     160  40  24° C 1.5128                           1146                                                                              Olive oil                                                                            ##STR872##     160  40  23° C 1.5124                           1147                                                                              Linseed oil                                                                          ##STR873##     160  40  23° C 1.5123                           1148                                                                              Rapeseed oil                                                                         ##STR874##                                                                               *    200  20  24° C 1.5122                           1149                                                                              Rice bran oil                                                                        ##STR875##     160  36  23° C 1.5133                           1150                                                                              Chrysalis oil                                                                        ##STR876##     160  36  23° C 1.5120                           1151                                                                              Flatfish oil                                                                         ##STR877##     160  40  23° C 1.5122                           1152                                                                              Shark oil                                                                            ##STR878##     160  40  22° C 1.5139                           1153                                                                              Whale oil                                                                            ##STR879##     170  40  22° C 1.5128                           1154                                                                              Cuttle- fish oil                                                                     ##STR880##                                                                               *    200  8   23° C 1.5133                           1155                                                                              Sardine oil                                                                          ##STR881##     170  40  23° C 1.5232                           1156                                                                              Mackerel oil                                                                         ##STR882##     170  40  24° C 1.5139                           1157                                                                              Saury- pike oil                                                                      ##STR883##     170  40  24° C 1.5146                           1158                                                                              Herring oil                                                                          ##STR884##     170  37  24° C 1.5120                           1159                                                                              Saurel oil                                                                           ##STR885##     170  36  25° C 1.5145                           1160                                                                              Menhaden oil                                                                         ##STR886##     170  37  25° C 1.5155                           1161                                                                              Cod oil                                                                              ##STR887##     160  40  23° C 1.5140                           1162                                                                              Liver oil                                                                            ##STR888##     160  40  24° C 1.5220                           1163                                                                              Menuke oil                                                                           ##STR889##     170  35  25° C 1.5127                           1164                                                                              Residual oil                                                                         ##STR890##     170  35  24° C 1.5130                           __________________________________________________________________________      *In an autoclave                                                         

EXAMPLE 1165

To a mixture of 150 g. of α-methyl-p-nitrobenzylamine, 100 ml. of anhydrous ether and 8 g. of trimethylamine was added a solution of 30 g. of linoleic acid chloride in 50 ml. of anhydrous ether, under stirring at 0°-5° C. The reaction mixture was boiled for 2 hours after addition. Subsequently, the ether solution of the reaction product was washed with acid, alkali and water to obtain 38.2 g. of a desired product, b.p. 209°-218° C./0.05 mmHg, n_(D) ²⁶ 1.5120. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       72.86          73.06                                               H (%)        9.41           9.66                                               N (%)        6.54           6.28                                               ______________________________________                                    

Examples 1166-1196 are shown in the following table:

    __________________________________________________________________________                                            C %     H %     N %                                                            Theo-                                                                              Ana-                                                                               Theo-                                                                              Ana-                                                                                Theo-                                                                             Ana-                Ex.                                                                               RCOA (A)                            reti-                                                                              lyti-                                                                              reti-                                                                              lyti-                                                                              reti-                                                                              lyti-               No.                                                                               Acid   Amine      Agent Solvent                                                                            n.sub.D cal cal cal cal cal cal                 __________________________________________________________________________     1166                                                                              Oleic acid                                                                          (Cl)                                                                              ##STR891##                                                                               Sodium- carbonate                                                                    Water- ace- tone                                                                   23° C                                                                       1.5120                                                                             72.93                                                                              73.20                                                                              9.97                                                                               10.01                                                                              6.30                                                                               6.19                1167                                                                              Lino- lenic  acid                                                                   (Cl)                                                                              ##STR892##                                                                               Pyridine                                                                             Tetra- hydro- furan                                                                23" 1.5005                                                                             73.60                                                                              73.79                                                                              9.15                                                                               9.40                                                                               6.36                                                                               6.23                1168                                                                              Lino- leic  acid                                                                    (Cl)                                                                              ##STR893##                                                                               Sodium- carbonate                                                                    Water- tetra- hydro- furan                                                         21.5"                                                                              1.5155                                                                             73.26                                                                              73.56                                                                              9.56                                                                               9.72                                                                               6.33                                                                               6.19                1169                                                                              Lino- leic  acid                                                                    (Cl)                                                                              ##STR894##                                                                               Sodium hydro- xide                                                                   Water- di- oxane                                                                   21" 1.5116                                                                             72.86                                                                              72.94                                                                              9.41                                                                               9.63                                                                               6.54                                                                               6.47                1170                                                                              Iso- stearic acid                                                                   (Cl)                                                                              ##STR895##                                                                               Pyridine                                                                             Ether                                                                              20" 1.5152                                                                             72.18                                                                              72.32                                                                              10.25                                                                              10.51                                                                              6.48                                                                               6.46                1171                                                                              Iso- stearic  acid                                                                  (Cl)                                                                              ##STR896##                                                                               Picoline                                                                             Ben- zene                                                                          23" 1.5160                                                                             72.18                                                                              72.31                                                                              10.25                                                                              10.49                                                                              6.48                                                                               6.32                1172                                                                              Saf- flower  oil acid                                                               (Cl)                                                                              ##STR897##                                                                               Trimethyl- amine                                                                     Ben- zene                                                                          24" 1.5137                                      1173                                                                              Soy- bean oil acid                                                                  (Cl)                                                                              ##STR898##                                                                               Triethyl- amine                                                                      Ether                                                                              20" 1.5123                                      1174                                                                              Sesame oil acid                                                                     (Cl)                                                                              ##STR899##                                                                               Dimethyl- amine                                                                      Ben- zene                                                                          24" 1.5094                                      1175                                                                              Castor oil acid                                                                     (Cl)                                                                              ##STR900##                                                                               Potassium hydroxide                                                                   ##STR901##                                                                        23" 1.5121                                      1176                                                                              Corn oil acid                                                                       (Cl)                                                                              ##STR902##                                                                               Potassium hydroxide                                                                  Water- di- oxane                                                                   22" 1.5115                                      1177                                                                              Cotton- seed oil acid                                                               (Cl)                                                                              ##STR903##                                                                               Sodium carbonate                                                                     Water- ace- tone                                                                   22" 1.5130                                      1178                                                                              Olive  oil acid                                                                     (Cl)                                                                              ##STR904##                                                                               Sodium carbonate                                                                      ##STR905##                                                                        23" 1.5123                                      1179                                                                              Lin- seed oil acid                                                                  (Cl)                                                                              ##STR906##                                                                               Pyridine                                                                             Ether                                                                              24" 1.5119                                      1180                                                                              Rape- seed  oil acid                                                                (Cl)                                                                              ##STR907##                                                                               Trimethyl- amine                                                                     Ether                                                                              23" 1.5134                                      1181                                                                              Rice bran oil acid                                                                  (Cl)                                                                              ##STR908##                                                                               Trimethyl- amine                                                                     Ben- zene                                                                          24" 1.5119                                      1182                                                                              Chrys- alis  oil acid                                                               (Cl)                                                                              ##STR909##                                                                               Pyridine                                                                             Ben- zene                                                                          22" 1.5118                                      1183                                                                              Flatfish oil acid                                                                   (Cl)                                                                              ##STR910##                                                                               Pyridine                                                                             Tetra- hydro- furan                                                                22" 1.5120                                      1184                                                                              Shark oil acid                                                                      (Cl)                                                                              ##STR911##                                                                               Picoline                                                                             Ben- zene                                                                          20" 1.5138                                      1185                                                                              Whale oil acid                                                                      (Cl)                                                                              ##STR912##                                                                               Lutidine                                                                             Tol- uene                                                                          21" 1.5128                                      1186                                                                              Cuttle- fish oil acid                                                               (Cl)                                                                              ##STR913##                                                                               Trimethyl- amine                                                                     Ether                                                                              22° C                                                                       1.5130                                      1187                                                                              Sardine oil acid                                                                    (Cl)                                                                              ##STR914##                                                                               Potassium carbonate                                                                  Ace- tone                                                                          23" 1.5221                                      1188                                                                              Mack- erel oil acid                                                                 (Cl)                                                                              ##STR915##                                                                               Pyridine                                                                             Ben- zene                                                                          24" 1.5146                                      1189                                                                              Saury- pike oil acid                                                                (Cl)                                                                              ##STR916##                                                                               Pyridine                                                                             Ace- tone                                                                          22" 1.5149                                      1190                                                                              Herring oil acid                                                                    (Cl)                                                                              ##STR917##                                                                               Potassium carbonate                                                                  Ace- tone                                                                          24" 1.5118                                      1191                                                                              Saurel oil acid                                                                     (Cl)                                                                              ##STR918##                                                                               Pyridine                                                                             Ben- zene                                                                          24" 1.5139                                      1192                                                                              Men- haden oil acid                                                                 (Cl)                                                                              ##STR919##                                                                               Potassium carbonate                                                                  Ace- tone                                                                          23" 1.5159                                      1193                                                                              Cod oil acid                                                                        (Cl)                                                                              ##STR920##                                                                               Trimethyl- amine                                                                     Tol- uene                                                                          22" 1.5139                                      1194                                                                              Liver oil acid                                                                      (Cl)                                                                              ##STR921##                                                                               Sodium hydroxide                                                                     Water- di-  oxane                                                                  23" 1.5220                                      1195                                                                              Menuke oil acid                                                                     (Cl)                                                                              ##STR922##                                                                               Potassium carbonate                                                                   ##STR923##                                                                        22" 1.5130                                      1196                                                                              Resi- dual oil acid                                                                 (Cl)                                                                              ##STR924##                                                                               Pyridine                                                                             Ether                                                                              24" 1.5135                                      __________________________________________________________________________

EXAMPLE 1196

Isostearic acid (34.4 g.) and 9.9 g. of cyclohexylamine were individually dissolved in 30 ml. of dioxane. The solutions were added with stirring at room temperature to a solution of 26.1 g. of dicyclohexyl carbodiimide in 30 ml. of dioxane, and the mixed solution was allowed to stand at room temperature for 8 hours. The solution was charged with 5 ml. of acetic acid and was again allowed to stand for additional 2 hours. Thereafter, dicyclohexylurea was separated by filtration and the filtrate was concentrated. The residue was dissolved in 100 ml. of ether and the ether solution was washed with 5% HCl, 5% NaOH and water, and was then dried over anhydrous sodium sulfate and concentrated and distilled to obtain 36.2 g. of a desired product, b.p. 200°-207° C./0.07 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       78.84          79.04                                               H (%)       12.96          12.63                                               N (%)        3.83           3.79                                               ______________________________________                                    

Examples 1197-1238 are shown in the following table:

    __________________________________________________________________________                       B                                                                              Condensing    C %       H %       N %                        __________________________________________________________________________     Example           Agent         Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-                                                                              Theor-                                                                              Analy-                No.  Amine        BBCNB  Solvent                                                                               tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                 __________________________________________________________________________     1197                                                                                 ##STR925##                                                                                  ##STR926##                                                                           Ether  77.48                                                                               77.29                                                                               13.32                                                                               13.09                                                                               4.30 4.35                  1198                                                                                 ##STR927##                                                                                  ##STR928##                                                                           Ether  77.10                                                                               76.83                                                                               13.27                                                                               13.08                                                                               4.50 4.48                  1199 NH.sub.2 CH.sub.2 CHCH.sub.2                                                                 ##STR929##                                                                           Ether  77.95                                                                               77.77                                                                               12.77                                                                               12.57                                                                               4.33 4.16                  1200 NH(CH.sub.2 CHCH.sub.2).sub.2                                                                ##STR930##                                                                           Tetrahydro- furan                                                                     79.27                                                                               78.94                                                                               12.47                                                                               12.09                                                                               3.85 3.67                  1201                                                                                 ##STR931##                                                                                  ##STR932##                                                                           Dioxane                                                                               78.56                                                                               78.31                                                                               12.90                                                                               12.76                                                                               3.98 3.79                  1202                                                                                 ##STR933##                                                                                  ##STR934##                                                                           Dioxane                                                                               79.09                                                                               78.73                                                                               13.01                                                                               12.84                                                                               3.69 3.44                  1203                                                                                 ##STR935##                                                                                  ##STR936##                                                                           Benzene                                                                               79.09                                                                               79.41                                                                               13.01                                                                               12.76                                                                               3.69 3.87                  1204                                                                                 ##STR937##                                                                                  ##STR938##                                                                           Ligroin                                                                               75.53                                                                               75.04                                                                               12.41                                                                               12.26                                                                               3.67 3.65                  1205                                                                                 ##STR939##                                                                                  ##STR940##                                                                           Toluene                                                                               75.89                                                                               75.53                                                                               12.48                                                                               12.28                                                                               3.54 3.16                  1206                                                                                 ##STR941##                                                                                  ##STR942##                                                                           Dioxane                                                                               82.70                                                                               82.98                                                                               10.41                                                                               10.33                                                                               3.22 3.09                  1207                                                                                 ##STR943##                                                                                  ##STR944##                                                                           Benzene                                                                               80.37                                                                               80.17                                                                               11.60                                                                               11.49                                                                               3.75 3.48                  1208                                                                                 ##STR945##                                                                                  ##STR946##                                                                           Dioxane- Pyridine                                                                     80.90                                                                               81.05                                                                               11.88                                                                               11.56                                                                               3.37 3.02                  1209                                                                                 ##STR947##                                                                                  ##STR948##                                                                           Dioxane                                                                               80.15                                                                               79.78                                                                               11.49                                                                               11.22                                                                               3.90 3.77                  1210                                                                                 ##STR949##                                                                                  ##STR950##                                                                           Ligroin                                                                               73.61                                                                               72.30                                                                               10.30                                                                               10.08                                                                               3.43 3.40                  1211                                                                                 ##STR951##                                                                                  ##STR952##                                                                           Acetone                                                                               76.39                                                                               76.59                                                                               10.61                                                                               10.23                                                                               3.71 3.69                  1212                                                                                 ##STR953##                                                                                  ##STR954##                                                                           Benzene                                                                               65.75                                                                               65.49                                                                                9.13                                                                                9.06                                                                               3.19 3.00                  1213                                                                                 ##STR955##                                                                                  ##STR956##                                                                           Tetra- hydro- furan                                                                   70.25                                                                               70.06                                                                                9.36                                                                                9.08                                                                               3.27 3.06                  1214                                                                                 ##STR957##                                                                                  ##STR958##                                                                           Dioxane                                                                               77.07                                                                               76.83                                                                               11.13                                                                               11.00                                                                               3.60 3.33                  1215                                                                                 ##STR959##                                                                                  ##STR960##                                                                           Toluene                                                                               77.36                                                                               77.14                                                                               11.24                                                                               10.98                                                                               3.47 3.09                  1216                                                                                 ##STR961##                                                                                  ##STR962##                                                                           Ether  78.27                                                                               78.00                                                                               12.84                                                                               12.73                                                                               4.15 4.07                  1217                                                                                 ##STR963##                                                                                  ##STR964##                                                                           Dioxane                                                                               78.56                                                                               78.24                                                                               12.90                                                                               12.71                                                                               3.98 3.78                  1218                                                                                 ##STR965##                                                                                  ##STR966##                                                                           Tetra- hydro- furan                                                                   74.73                                                                               74.99                                                                               12.26                                                                               12.05                                                                               3.96 3.74                  1219                                                                                 ##STR967##                                                                                  ##STR968##                                                                           Benzene                                                                               78.84                                                                               78.82                                                                               12.96                                                                               13.15                                                                               3.83 3.58                  1220                                                                                 ##STR969##                                                                                  ##STR970##                                                                           Dioxane                                                                               80.37                                                                               80.05                                                                               11.60                                                                               11.40                                                                               3.75 3.36                  1221                                                                                 ##STR971##                                                                                  ##STR972##                                                                           Chloro- form                                                                          82.88                                                                               83.09                                                                               10.65                                                                               10.33                                                                               3.02 3.20                  1222                                                                                 ##STR973##                                                                                  ##STR974##                                                                           Chloro- form                                                                          80.47                                                                               80.22                                                                               12.83                                                                               12.49                                                                               3.13 3.03                  1223                                                                                 ##STR975##                                                                                  ##STR976##                                                                           Dioxane                                                                               80.56                                                                               80.19                                                                               11.70                                                                               11.46                                                                               3.61 3.39                  1224                                                                                 ##STR977##                                                                                  ##STR978##                                                                           Chloro- form                                                                          81.14                                                                               81.04                                                                               11.35                                                                               11.05                                                                               3.51 3.46                  1225                                                                                 ##STR979##                                                                                  ##STR980##                                                                           Dioxane                                                                               77.07                                                                               76.87                                                                               11.13                                                                               11.02                                                                               3.60 3.48                  1226                                                                                 ##STR981##                                                                                  ##STR982##                                                                           Chloro- form                                                                          80.56                                                                               80.34                                                                               11.70                                                                               11.44                                                                               3.61 3.49                  1227                                                                                 ##STR983##                                                                                  ##STR984##                                                                           Ether  80.56                                                                               80.44                                                                               11.70                                                                               11.49                                                                               3.61 3.50                  1228                                                                                 ##STR985##                                                                                  ##STR986##                                                                           Dioxane                                                                               77.36                                                                               77.08                                                                               11.24                                                                               11.05                                                                               3.47 3.30                  1229                                                                                 ##STR987##                                                                                  ##STR988##                                                                           Tetra- hydro- furan                                                                   77.36                                                                               77.00                                                                               11.24                                                                               11.04                                                                               3.47 3.59                  1230                                                                                 ##STR989##                                                                                  ##STR990##                                                                           Toluene                                                                               76.22                                                                               76.49                                                                               12.55                                                                               12.33                                                                               3.42 3.62                  1231 NH.sub.2 C.sub.12 H.sub.25                                                                   ##STR991##                                                                           Benzene                                                                               80.11                                                                               79.87                                                                               13.22                                                                               13.04                                                                               3.11 3.00                  1232                                                                                 ##STR992##                                                                                  ##STR993##                                                                           Ether  75.89                                                                               75.59                                                                               12.48                                                                               12.06                                                                               3.54 3.62                  1233                                                                                 ##STR994##                                                                                  ##STR995##                                                                           Ether  70.25                                                                               69.93                                                                                9.36                                                                                8.99                                                                               3.27 3.49                  1234                                                                                 ##STR996##                                                                                  ##STR997##                                                                           Toluene                                                                               80.56                                                                               80.28                                                                               11.70                                                                               11.56                                                                               3.61 3.38                  1235                                                                                 ##STR998##                                                                                  ##STR999##                                                                           Tetra- hydro- furan                                                                   77.07                                                                               76.85                                                                               11.13                                                                               10.78                                                                               3.60 3.29                  1236                                                                                 ##STR1000##                                                                                 ##STR1001##                                                                          Benzene                                                                               73.61                                                                               73.49                                                                               10.30                                                                               10.06                                                                               3.43 3.06                  1237                                                                                 ##STR1002##                                                                                 ##STR1003##                                                                          Dioxane                                                                               73.18                                                                               72.94                                                                               10.16                                                                               10.00                                                                               3.55 3.50                  __________________________________________________________________________

EXAMPLE 1238

A mixture of 10 g. of isostearic acid, 5 g. of cyclohexylamine, 0.2 g. of p-toluenesulfonic acid and 100 ml. of toluene was heated for 8 hours using a water separator. The reaction product was treated according to ordinary procedures to obtain 12.3 g. of a desired product, b.p. 200°-204° C./0.06 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       78.84          79.06                                               H (%)       12.96          12.83                                               N (%)        3.83           3.78                                               ______________________________________                                    

EXAMPLE 1239

To a solution of 14.2 g. of isostearic acid and 5.5 g. of triethylamine in 100 cc. of tetrahydrofuran was added 5.9 g. of ethyl chloroformate under stirring at -10° to -5° C. The stirring was continued at -5° C. for additional 20 minutes. Subsequently, 6.0 g. of α-methylbenzylamine was added dropwise with stirring at -5° C. After the addition, the cooling both was removed and the temperature was gradually elevated and the stirring was continued. Thereafter, the temperature was gradually increased and the reaction mixture was stirred at 40° C. for 20 minutes. After cooling, the tetrahydrofuran was distilled off in vacuo and the residue was dissolved in ether. The ether solution was washed with cold dilute hydrochloric acid, cold sodium carbonate water and water, and was then dried with anhydrous sodium carbonate. The ether was removed by distillation and the residue was distilled in vacuo to obtain 15.5 g. of a desired product, b.p. 200°-207° C./0.02 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.56          80.71                                               H (%)       11.70          11.70                                               N (%)        3.61           3.58                                               ______________________________________                                    

Examples 1240-1307 are shown in the following table:

    __________________________________________________________________________     Example                b.p.   Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                    No.  Amine             ° C./mmHg.                                                                     tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical                     __________________________________________________________________________     1240                                                                                 ##STR1004##      190-205/0.03                                                                          77.48                                                                               77.57                                                                              13.32                                                                               13.64                                                                              4.30 4.25                      1241 NH.sub.2 C.sub.12 H.sub.25                                                                       Semi-solid                                                                            60.11                                                                               80.25                                                                              13.22                                                                               13.42                                                                              3.11 3.05                      1242 NH.sub.2 CH.sub.2 CHCH.sub.2                                                                     192-199/0.04                                                                          77.95                                                                               78.20                                                                              12.77                                                                               12.89                                                                              4.33 4.07                      1243                                                                                 ##STR1005##      188-194/0.04                                                                          77.10                                                                               77.25                                                                              13.27                                                                               13.42                                                                              4.50 4.46                      1244                                                                                 ##STR1006##      192-203/0.02                                                                          79.27                                                                               79.44                                                                              12.47                                                                               12.54                                                                              3.85 3.68                      1245                                                                                 ##STR1007##      200-208/0.06                                                                          78.58                                                                               78.63                                                                              12.90                                                                               13.00                                                                              3.98 3.89                      1246                                                                                 ##STR1008##      200-204/0.06                                                                          78.84                                                                               78.95                                                                              12.96                                                                               13.04                                                                              5.83 3.89                      1247                                                                                 ##STR1009##      202-207/0.05                                                                          79.09                                                                               79.20                                                                              13.01                                                                               13.43                                                                              3.69 3.52                      1255                                                                                 ##STR1010##      202-210/0.04                                                                          75.89                                                                               75.94                                                                              12.48                                                                               12.55                                                                              3.54 3.54                      1256                                                                                 ##STR1011##      203-212/0.05                                                                          75.89                                                                               75.95                                                                              12.48                                                                               12.58                                                                              3.54 3.45                      1257                                                                                 ##STR1012##      202-209/0.05                                                                          75.89                                                                               76.04                                                                              12.48                                                                               12.64                                                                              3.54 3.49                      1258                                                                                 ##STR1013##      200-214/0.07                                                                          76.22                                                                               76.14                                                                              12.55                                                                               12.63                                                                              3.42 3.40                      1259                                                                                 ##STR1014##      204-210/0.06                                                                          80.37                                                                               80.42                                                                              11.60                                                                               11.58                                                                              3.75 3.52                      1260                                                                                 ##STR1015##      202-218/0.05                                                                          80.37                                                                               80.53                                                                              11.60                                                                               11.69                                                                              3.75 3.73                      1261                                                                                 ##STR1016##      202-207/0.05                                                                          80.37                                                                               80.38                                                                              11.60                                                                               11.78                                                                              3.75 3.55                      1262                                                                                 ##STR1017##      205-214/0.06                                                                          80.90                                                                               81.16                                                                              11.88                                                                               11.98                                                                              3.37 3.38                      1263                                                                                 ##STR1018##      210-215/0.06                                                                          80.15                                                                               80.29                                                                              11.49                                                                               11.64                                                                              3.90 3.84                      1264                                                                                 ##STR1019##      211-217/0.05                                                                          80.15                                                                               80.37                                                                              11.49                                                                               11.58                                                                              3.90 3.88                      1265                                                                                 ##STR1020##      205-214/0.07                                                                          73.18                                                                               73.44                                                                              10.16                                                                               10.27                                                                              3.55 3.49                      1266                                                                                 ##STR1021##      204-218/0.06                                                                          73.18                                                                               73.07                                                                              10.16                                                                               10.32                                                                              3.55 3.46                      1267                                                                                 ##STR1022##      202-214/0.06                                                                          73.18                                                                               73.21                                                                              10.16                                                                               10.54                                                                              3.55 3.39                      1268                                                                                 ##STR1023##      204-208/0.06                                                                          65.75                                                                               65.85                                                                               9.13                                                                                9.29                                                                              3.19 3.08                      1269                                                                                 ##STR1024##      199-204/0.04                                                                          76.39                                                                               76.48                                                                              10.61                                                                               10.88                                                                              3.71 3.52                      1270                                                                                 ##STR1025##      204-214/0.05                                                                          73.61                                                                               73.80                                                                              10.30                                                                               10.52                                                                              3.43 3.36                      1271                                                                                 ##STR1026##      202-208/0.04                                                                          70.25                                                                               70.45                                                                               9.36                                                                               9.62                                                                               3.27 3.19                      1272                                                                                 ##STR1027##      208-214/0.03                                                                          70.25                                                                               70.40                                                                               9.36                                                                               9.48                                                                               3.25 3.05                      1273                                                                                 ##STR1028##      206-214/0.06                                                                          73.61                                                                               73.87                                                                              10.30                                                                               10.45                                                                              3.43 3.38                      1274                                                                                 ##STR1029##      200-213/0.05                                                                          79.09                                                                               79.30                                                                              13.01                                                                               13.07                                                                              3.69 3.56                      1275                                                                                 ##STR1030##      204-223/0.05                                                                          82.70                                                                               82.65                                                                              10.41                                                                               10.65                                                                              3.22 3.18                      1276                                                                                 ##STR1031##      203-208/0.05                                                                          77.07                                                                               77.14                                                                              11.13                                                                               11.24                                                                              3.63 5.58                      1277                                                                                 ##STR1032##      201-209/0.05                                                                          77.07                                                                               77.18                                                                              11.13                                                                               11.28                                                                              3.60 3.42                      1278                                                                                 ##STR1033##      200-212/0.05                                                                          77.07                                                                               77.35                                                                              11.13                                                                               11.26                                                                              3.60 3.49                      1279                                                                                 ##STR1034##      204-214/0.04                                                                          77.36                                                                               77.41                                                                              11.24                                                                               11.65                                                                              3.47 3.46                      1280                                                                                 ##STR1035##      200-220/0.08                                                                          77.36                                                                               77.48                                                                              11.24                                                                               11.36                                                                              3.47 3.38                      1281                                                                                 ##STR1036##      199-209/0.08                                                                          77.36                                                                               77.45                                                                              11.24                                                                               11.28                                                                              3.47 3.24                      1282                                                                                 ##STR1037##      203-208/0.04                                                                          78.27                                                                               78.50                                                                              12.84                                                                               12.99                                                                              4.15 3.98                      1283                                                                                 ##STR1038##      200-208/0.05                                                                          78.56                                                                               78.74                                                                              12.90                                                                               13.08                                                                              3.98 3.89                      1284                                                                                 ##STR1039##      200-215/0.05                                                                          78.84                                                                               78.82                                                                              12.96                                                                               13.08                                                                              3.83 3.45                      1285                                                                                 ##STR1040##      206-214/0.06                                                                          74.73                                                                               74.92                                                                              12.26                                                                               12.57                                                                              3.96 3.64                      1286                                                                                 ##STR1041##      201-208/0.05                                                                          80.37                                                                               80.64                                                                              11.60                                                                               11.84                                                                              3.75 3.50                      1287                                                                                 ##STR1042##      218-225/0.06                                                                          82.88                                                                               82.98                                                                              10.65                                                                               10.90                                                                              3.02 3.00                      1288                                                                                 ##STR1043##      201-212/0.05                                                                          80.56                                                                               80.75                                                                              11.70                                                                               11.92                                                                              3.61 3.38                      1289                                                                                 ##STR1044##      203-208/0.05                                                                          81.14                                                                               81.24                                                                              11.35                                                                               11.48                                                                              3.51 3.58                      1290                                                                                 ##STR1045##      214-219/0.04                                                                          77.07                                                                               77.26                                                                              11.13                                                                               11.25                                                                              3.60 3.47                      1291                                                                                 ##STR1046##      209-219/0.05                                                                          77.07                                                                               77.26                                                                              11.13                                                                               11.34                                                                              3.60 3.45                      1292                                                                                 ##STR1047##      205-217/0.05                                                                          77.36                                                                               77.49                                                                              11.24                                                                               11.26                                                                              3.47 3.38                      1293                                                                                 ##STR1048##      205-214/0.04                                                                          77.36                                                                               77.50                                                                              11.24                                                                               11.37                                                                              3.47 3.37                      1294                                                                                 ##STR1049##      203-218/0.05                                                                          77.36                                                                               77.49                                                                              11.24                                                                               11.48                                                                              3.47 3.44                      1295                                                                                 ##STR1050##      208-218/0.05                                                                          77.64                                                                               77.64                                                                              11.34                                                                               11.34                                                                              3.35 3.27                      1296                                                                                 ##STR1051##      200-215/0.05                                                                          80.56                                                                               80.74                                                                              11.70                                                                               11.90                                                                              3.61 3.66                      1297                                                                                 ##STR1052##      200-208/0.04                                                                          80.56                                                                               80.74                                                                              11.70                                                                               11.86                                                                              3.61 3.45                      1298                                                                                 ##STR1053##      200-205/0.04                                                                          80.56                                                                               80.58                                                                              11.70                                                                               11.94                                                                              3.61 3.36                      1299                                                                                 ##STR1054##      200-218/0.05                                                                          80.37                                                                               80.39                                                                              11.60                                                                               11.63                                                                              3.75 3.65                      1300                                                                                 ##STR1055##      201-208/0.02                                                                          80.73                                                                               80.82                                                                              11.80                                                                               11.94                                                                              3.49 3.15                      1301                                                                                 ##STR1056##      203-207/0.04                                                                          80.73                                                                               80.71                                                                              11.80                                                                               12.05                                                                              3.49 3.38                      1302                                                                                 ##STR1057##      200-218/0.05                                                                          73.61                                                                               73.88                                                                              10.30                                                                               10.56                                                                              3.43 3.34                      1303                                                                                 ##STR1058##      200-216/0.05                                                                          73.61                                                                               73.74                                                                              10.30                                                                               10.49                                                                              3.43 3.36                      1304                                                                                 ##STR1059##      200-214/0.05                                                                          76.39                                                                               73.61                                                                              10.61                                                                               10.88                                                                              8.71 3.48                      1305                                                                                 ##STR1060##      200-215/0.05                                                                          65.75                                                                               65.86                                                                               9.13                                                                                9.23                                                                              3.19 3.47                      1306                                                                                 ##STR1061##      200-218/0.05                                                                          73.61                                                                               73.75                                                                              10.30                                                                               10.49                                                                              3.43 3.18                      1307                                                                                 ##STR1062##      215-223/0.06                                                                          80.51                                                                               80.78                                                                              12.31                                                                               12.40                                                                              3.35 3.06                      __________________________________________________________________________

EXAMPLE 1308

To a mixture of 5 g. of cyclohexylamine, 2.5 g. of trimethylamine and 50 ml. of anhydrous ether was added 10 g. of isostearic acid chloride dropwise at O°-5° C. The reaction mixture was stirred at room temperature for about 10 hours and boiled for 2 hours. Subsequently, the ether layer was washed with acid, alkali and water and was then dried, concentrated and distilled to obtain 11.9 g. of a desired product, b.p. 200°-203° C./0.05 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       77.48          77.58                                               H (%)       13.32          13.41                                               N (%)        4.32           4.16                                               ______________________________________                                    

Examples 1309-1386 are shown in the following table, in which:

Condensation assistant:

a. NaOH

b. KOH

c. Na₂ CO₃

d. K₂ CO₃

e. Trimethylamine

f. Pyridine

g. Excess amine

h. Anion exchange resin IRA-400

Solvent:

A. acetone

B. methylisobutylketone

C. ether

D. tetrahydrofuran

E. dioxane

F. benzene

G. toluene

H. water

I. pyridine

    __________________________________________________________________________                                      C %       H %       N %                       __________________________________________________________________________     Ex.            Condensing b.p.   Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-               No.                                                                                Amine      agent Solvent                                                                             ° C./mmHg                                                                      tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                __________________________________________________________________________     1309                                                                               ##STR1063##                                                                               a     A    190-203/0.03                                                                          77.48                                                                               77.39                                                                               13.32                                                                               13.61                                                                               4.30 4.18                 1310                                                                              NH.sub.2 C.sub.12 H.sub.25                                                                 g     B    Semisolid                                                                             80.11                                                                               80.35                                                                               13.22                                                                               13.40                                                                               3.11 3.06                 1311                                                                              NH.sub.2 CH.sub.2CCH.sub.2                                                                 g     B    191-199/0.04                                                                          77.95                                                                               78.21                                                                               12.77                                                                               12.89                                                                               4.33 4.09                 1312                                                                               ##STR1064##                                                                               g     C    188-192/0.04                                                                          77.10                                                                               77.23                                                                               13.27                                                                               13.41                                                                               4.50 4.40                 1313                                                                               ##STR1065##                                                                               g     F    192-208/0.02                                                                          79.27                                                                               79.41                                                                               12.47                                                                               12.52                                                                               3.85 3.69                 1314                                                                               ##STR1066##      I    200-204/0.06                                                                          78.56                                                                               78.62                                                                               12.90                                                                               13.02                                                                               3.98 3.89                 1315                                                                               ##STR1067##                                                                               g     F    200-205/0.06                                                                          78.84                                                                               78.96                                                                               12.96                                                                               13.05                                                                               3.83 3.79                 1316                                                                               ##STR1068##                                                                               d     B    202-207/0.05                                                                          79.09                                                                               79.21                                                                               13.01                                                                               13.42                                                                               3.69 3.32                 1317                                                                               ##STR1069##                                                                               e     C    210-222/0.05                                                                          80.47                                                                               80.61                                                                               12.83                                                                               12.93                                                                               3.13 3.09                 1318                                                                               ##STR1070##                                                                               f     I    202-209/0.05                                                                          79.09                                                                               79.31                                                                               13.01                                                                               13.21                                                                               3.69 3.50                 1319                                                                               ##STR1071##                                                                               f     I    204-211/0.05                                                                          79.09                                                                               79.20                                                                               13.01                                                                               13.03                                                                               3.69 3.58                 1320                                                                               ##STR1072##                                                                               f     B    203-211/0.05                                                                          79.09                                                                               79.23                                                                               13.01                                                                               13.05                                                                               3.69 3.57                 1321                                                                               ##STR1073##                                                                               f     C    200-206/0.04                                                                          75.53                                                                               75.62                                                                               12.41                                                                               12.59                                                                               3.67 3.45                 1322                                                                               ##STR1074##                                                                               b     HD   201-207/0.04                                                                          75.53                                                                               75.65                                                                               12.41                                                                               12.43                                                                               3.67 3.54                 1323                                                                               ##STR1075##                                                                               c     B    200-208/0.05                                                                          75.53                                                                               75.57                                                                               12.41                                                                               12.57                                                                               3.67 3.62                 1324                                                                               ##STR1076##                                                                               d     B    201-210/0.04                                                                          75.89                                                                               75.94                                                                               12.48                                                                               12.57                                                                               3.54 3.53                 1325                                                                               ##STR1077##                                                                               d     HA   203-211/0.05                                                                          75.89                                                                               75.96                                                                               12.48                                                                               12.68                                                                               3.54 3.45                 1326                                                                               ##STR1078##                                                                               f     I    202-209/0.05                                                                          75.89                                                                               76.01                                                                               12.48                                                                               12.61                                                                               3.54 3.48                 1327                                                                               ##STR1079##                                                                               f     I    200-214/0.08                                                                          76.22                                                                               76.24                                                                               12.55                                                                               12.64                                                                               3.42 3.34                 1328                                                                               ##STR1080##                                                                               h     F    204-211/0.06                                                                          80.37                                                                               80.52                                                                               11.60                                                                               11.68                                                                               3.75 3.62                 1329                                                                               ##STR1081##                                                                               f     F    202-210/0.05                                                                          80.37                                                                               80.63                                                                               11.60                                                                               11.79                                                                               3.75 3.63                 1330                                                                               ##STR1082##                                                                               f     G    202-211/0.05                                                                          80.37                                                                               80.33                                                                               11.60                                                                               11.75                                                                               3.75 3.25                 1331                                                                               ##STR1083##                                                                               f     C    205-215/0.05                                                                          80.90                                                                               81.26                                                                               11.88                                                                               11.97                                                                               3.37 3.33                 1332                                                                               ##STR1084##                                                                               h     E    210-216/0.06                                                                          80.15                                                                               80.39                                                                               11.49                                                                               11.62                                                                               3.90 3.81                 1333                                                                               ##STR1085##                                                                               f     D    211-219/0.05                                                                          80.15                                                                               80.39                                                                               11.49                                                                               11.55                                                                               3.90 3.88                 1334                                                                               ##STR1086##                                                                               h     F    203-214/0.07                                                                          73.18                                                                               73.44                                                                               10.16                                                                               10.29                                                                               3.55 3.40                 1335                                                                               ##STR1087##                                                                               e     F    204-213/0.06                                                                          73.18                                                                               73.47                                                                               10.16                                                                               10.31                                                                               3.55 3.40                 1336                                                                               ##STR1088##                                                                               h     C    202-213/0.06                                                                          73.18                                                                               73.31                                                                               10.16                                                                               10.64                                                                               3.55 3.38                 1337                                                                               ##STR1089##                                                                               e     C    204-218/0.06                                                                          65.75                                                                               65.96                                                                               9.13 9.29 3.19 3.09                 1338                                                                               ##STR1090##                                                                               h     C    199-204/0.04                                                                          76.39                                                                               76.58                                                                               10.61                                                                               10.83                                                                               3.71 3.54                 1339                                                                               ##STR1091##                                                                               e     C    204-211/0.05                                                                          73.61                                                                               73.82                                                                               10.30                                                                               10.51                                                                               3.43 3.37                 1340                                                                               ##STR1092##                                                                               h     F    202-215/0.04                                                                          70.25                                                                               70.65                                                                               9.36 9.62 3.27 3.07                 1341                                                                               ##STR1093##                                                                               e     C    203-214/0.03                                                                          70.25                                                                               70.41                                                                               9.36 9.45 3.25 3.06                 1342                                                                               ##STR1094##                                                                               e     F    205.sub.]214/0.06                                                                     73.61                                                                               73.87                                                                               10.30                                                                               10.45                                                                               3.43 3.39                 1343                                                                               ##STR1095##                                                                               e     G    200-223/0.05                                                                          79.09                                                                               79.34                                                                               13.01                                                                               13.09                                                                               3.69 3.46                 1344                                                                               ##STR1096##                                                                               e     B    201-223/0.05                                                                          82.70                                                                               82.43                                                                               10.41                                                                               10.68                                                                               3.22 3.09                 1345                                                                               ##STR1097##                                                                               a     A    203-209/0.05                                                                          77.07                                                                               77.24                                                                               11.13                                                                               11.25                                                                               3.63 3.58                 1346                                                                               ##STR1098##                                                                               b     H    201-209/0.05                                                                          77.07                                                                               77.19                                                                               11.13                                                                               11.29                                                                               3.60 3.41                 1347                                                                               ##STR1099##                                                                               a     HD   200-210/0.05                                                                          77.07                                                                               77.33                                                                               11.13                                                                               11.25                                                                               3.60 3.40                 1348                                                                               ##STR1100##                                                                               a     HD   201-214/0.04                                                                          77.36                                                                               77.51                                                                               11.24                                                                               11.63                                                                               3.47 3.36                 1349                                                                               ##STR1101##                                                                               a     HE   200-220/0.08                                                                          77.36                                                                               77.49                                                                               11.24                                                                               11.35                                                                               3.47 3.18                 1350                                                                               ##STR1102##                                                                               c     B    199-218/0.08                                                                          77.36                                                                               77.46                                                                               11.24                                                                               11.38                                                                               3.47 3.27                 1351                                                                               ##STR1103##                                                                               f     I    200-208/0.04                                                                          78.27                                                                               78.53                                                                               12.84                                                                               12.99                                                                               4.15 3.95                 1352                                                                               ##STR1104##                                                                               d     B    200-208/0.05                                                                          78.56                                                                               78.84                                                                               12.90                                                                               13.07                                                                               3.98 3.88                 1353                                                                               ##STR1105##                                                                               f     C    200-213/0.05                                                                          78.84                                                                               78.92                                                                               12.96                                                                               13.08                                                                               3.83 3.46                 1354                                                                               ##STR1106##                                                                               d     B    200-214/0.06                                                                          74.73                                                                               74.92                                                                               12.26                                                                               12.54                                                                               3.96 3.65                 1355                                                                               ##STR1107##                                                                               f     C    201-209/0.05                                                                          80.37                                                                               80.61                                                                               11.60                                                                               11.87                                                                               3.75 3.52                 1356                                                                               ##STR1108##                                                                               a     HE   218-223/0.06                                                                          82.88                                                                               82.90                                                                               10.65                                                                               10.94                                                                               3.02 3.00                 1357                                                                               ##STR1109##                                                                               f     F    201-212/0.05                                                                          80.56                                                                               80.76                                                                               11.70                                                                               11.92                                                                               3.61 3.38                 1358                                                                               ##STR1110##                                                                               b     HD   203-209/0.05                                                                          81.14                                                                               81.34                                                                               11.35                                                                               11.48                                                                               3.51 3.50                 1359                                                                               ##STR1111##                                                                               f     G    211-219/0.04                                                                          77.07                                                                               77.27                                                                               11.13                                                                               11.22                                                                               3.60 3.49                 1360                                                                               ##STR1112##                                                                               d     B    209-218/0.05                                                                          77.07                                                                               77.30                                                                               11.13                                                                               11.32                                                                               3.60 3.25                 1361                                                                               ##STR1113##                                                                               f     C    205-218/0.05                                                                          77.36                                                                               77.49                                                                               11.24                                                                               11.46                                                                               3.47 3.33                 1362                                                                               ##STR1114##                                                                               f     I    205-215/0.04                                                                          77.36                                                                               77.52                                                                               11.24                                                                               11.38                                                                               3.47 3.29                 1363                                                                               ##STR1115##                                                                               c     G    203-218/0.05                                                                          77.36                                                                               77.54                                                                               11.24                                                                               11.49                                                                               3.47 3.41                 1364                                                                               ##STR1116##                                                                               a     HE   206-219/0.05                                                                          77.64                                                                               77.66                                                                               11.34                                                                               11.38                                                                               3.35 3.29                 1365                                                                               ##STR1117##                                                                               c     HE   200-213/0.05                                                                          80.56                                                                               80.84                                                                               11.70                                                                               11.91                                                                               3.61 3.67                 1366                                                                               ##STR1118##                                                                               e     B    200-206/0.04                                                                          80.56                                                                               80.72                                                                               11.70                                                                               11.90                                                                               3.61 3.48                 1367                                                                               ##STR1119##                                                                               a     H    200-206/0.04                                                                          80.56                                                                               80.63                                                                               11.70                                                                               11.94                                                                               3.61 3.35                 1368                                                                               ##STR1120##                                                                               e     C    200-214/0.05                                                                          80.37                                                                               80.49                                                                               11.60                                                                               11.83                                                                               3.75 3.67                 1369                                                                               ##STR1121##                                                                               f     C    201-209/0.02                                                                          80.73                                                                               80.82                                                                               11.80                                                                               11.90                                                                               3.49 3.16                 1370                                                                               ##STR1122##                                                                               f     F    203-209/0.04                                                                          80.73                                                                               80.91                                                                               11.80                                                                               12.05                                                                               3.49 3.34                 1371                                                                               ##STR1123##                                                                               f     G    200-214/0.05                                                                          73.61                                                                               73.88                                                                               10.30                                                                               10.58                                                                               3.43 3.31                 1372                                                                               ##STR1124##                                                                               b     HA   200-217/0.05                                                                          73.61                                                                               73.79                                                                               10.30                                                                               10.49                                                                               3.43 3.30                 1373                                                                               ##STR1125##                                                                               f     C    200-211/0.05                                                                          76.39                                                                               73.62                                                                               10.61                                                                               10.87                                                                               3.71 3.49                 1374                                                                               ##STR1126##                                                                               f     C    200-213/0.05                                                                          65.75                                                                               65.85                                                                               9.13 9.43 3.19 3.48                 1375                                                                               ##STR1127##                                                                               f     C    200-215/0.05                                                                          73.61                                                                               73.76                                                                               10.30                                                                               10.66                                                                               3.43 3.19                 1376                                                                               ##STR1128##                                                                               b     HA   215-223/0.06                                                                          80.51                                                                               80.77                                                                               12.31                                                                               10.42                                                                               3.35 3.05                 __________________________________________________________________________

EXAMPLE 1377

A mixture of 10 g. of isostearic acid and 5 g. of cyclohexylamine was reacted with stirring at 150° C. for 39 hours removing water during the reaction. The reaction mixture was immediately distilled to obtain 11.5 g. of a desired product, b.p. 200°-206° C./0.08 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       78.84          79.06                                               H (%)       12.96          12.83                                               N (%)        3.83           3.78                                               ______________________________________                                    

Examples 1378-1428 are shown in the following table:

    __________________________________________________________________________                         Reaction                                                                  Reaction                                                                            temper-         C %      H %      N %                      Ex.            time ature                                                                               Auto-                                                                              b.p.   Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-              No.       Amine                                                                               (hr.)                                                                               (° C.)                                                                       clave                                                                              ° C./mmHg                                                                      tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical               __________________________________________________________________________     1378                                                                                      ##STR1129##                                                                        20   180  Used                                                                               187-201/0.05                                                                          77.48                                                                               77.68                                                                              13.32                                                                               13.09                                                                              4.30 4.18                1379                                                                                      ##STR1130##                                                                        50   200  Used                                                                               190-200/0.06                                                                          77.10                                                                               77.41                                                                              13.27                                                                               13.07                                                                              4.50 4.22                1380                                                                                      ##STR1131##                                                                        20   180  Used                                                                               193-204/0.06                                                                          77.95                                                                               78.26                                                                              12.77                                                                               12.51                                                                              4.33 4.10                1381                                                                                      ##STR1132##                                                                        50   200  Used                                                                               198-208/0.05                                                                          79.27                                                                               79.41                                                                              12.47                                                                               12.22                                                                              3.85 3.58                1382                                                                                      ##STR1133##                                                                        28   185  Used                                                                               200-207/0.05                                                                          78.56                                                                               78.78                                                                              12.90                                                                               12.77                                                                              3.98 3.64                1383                                                                                      ##STR1134##                                                                        38   150  None                                                                               200-212/0.06                                                                          79.09                                                                               79.15                                                                              13.01                                                                               12.89                                                                              3.69 3.43                1384                                                                                      ##STR1135##                                                                        27   160  --  205-212/0.07                                                                          77.09                                                                               79.23                                                                              13.01                                                                               12.86                                                                              3.69 3.45                1385                                                                                      ##STR1136##                                                                        25   160  --  202-209/0.07                                                                          79.09                                                                               79.22                                                                              13.01                                                                               12.91                                                                              3.69 3.42                1386                                                                                      ##STR1137##                                                                        25   160  --  200-210/0.05                                                                          79.09                                                                               79.31                                                                              13.01                                                                               12.37                                                                              3.69 3.53                1387                                                                                      ##STR1138##                                                                        28   185  --  205-213/0.06                                                                          75.89                                                                               76.02                                                                              12.48                                                                               12.40                                                                              3.54 3.28                1388                                                                                      ##STR1139##                                                                        30   185  --  203-214/0.05                                                                          75.89                                                                               76.04                                                                              12.48                                                                               12.28                                                                              3.54 3.37                1389                                                                                      ##STR1140##                                                                        29   185  --  200-218/0.05                                                                          75.89                                                                               76.00                                                                              12.48                                                                               12.19                                                                              3.54 3.31                1390                                                                                      ##STR1141##                                                                        29   185  --  203-209/0.04                                                                          76.22                                                                               76.40                                                                              12.55                                                                               12.28                                                                              3.42 3.10                1391                                                                                      ##STR1142##                                                                        29   185  --  200-211/0.05                                                                          75.53                                                                               75.75                                                                              12.41                                                                               12.06                                                                              3.67 3.37                1392                                                                                      ##STR1143##                                                                        29   185  --  200-209/0.05                                                                          75.53                                                                               75.80                                                                              12.41                                                                               12.38                                                                              3.67 3.43                1393                                                                                      ##STR1144##                                                                        32   180  --  199-208/0.06                                                                          80.37                                                                               80.46                                                                              11.60                                                                               11.41                                                                              3.75 3.52                1394                                                                                      ##STR1145##                                                                        32   180  --  200-211/0.06                                                                          80.37                                                                               80.54                                                                              11.60                                                                               11.43                                                                              3.75 3.56                1395                                                                                      ##STR1146##                                                                        32   180  --  200-213/0.06                                                                          80.37                                                                               80.63                                                                              11.60                                                                               11.34                                                                              3.75 3.79                1396                                                                                      ##STR1147##                                                                        30   185  --  210-231/0.04                                                                          80.15                                                                               80.43                                                                              11.49                                                                               11.29                                                                              3.90 3.47                1397                                                                                      ##STR1148##                                                                        30   185  --  208-222/0.04                                                                          80.15                                                                               80.33                                                                              11.49                                                                               11.31                                                                              3.90 3.90                1398                                                                                      ##STR1149##                                                                        30   185  --  200-208/0.05                                                                          77.07                                                                               77.39                                                                              11.13                                                                               11.50                                                                              3.60 3.62                1399                                                                                      ##STR1150##                                                                        29   185  --  201-209/0.06                                                                          77.07                                                                               77.25                                                                              11.13                                                                               11.00                                                                              3.60 3.43                1400                                                                                      ##STR1151##                                                                        33   185  --  202-211/0.06                                                                          77.07                                                                               77.28                                                                              11.13                                                                               10.87                                                                              3.60 3.59                1401                                                                                      ##STR1152##                                                                        33   185  --  201-209/0.05                                                                          77.36                                                                               77.60                                                                              11.24                                                                               10.94                                                                              3.47 3.04                1402                                                                                      ##STR1153##                                                                        30   185  --  201-213/0.06                                                                          77.36                                                                               77.54                                                                              11.24                                                                               10.02                                                                              3.47 3.30                1403                                                                                      ##STR1154##                                                                        42   185  --  203-214/0.07                                                                          77.36                                                                               77.55                                                                              11.24                                                                               10.02                                                                              3.47 3.29                1404                                                                                      ##STR1155##                                                                        32   185  --  199-210/0.05                                                                          76.39                                                                               76.61                                                                              10.61                                                                               10.41                                                                              3.71 3.56                1405                                                                                      ##STR1156##                                                                        31   185  --  195-208/0.05                                                                          73.18                                                                               73.30                                                                              10.16                                                                               10.04                                                                              3.55 3.30                1406                                                                                      ##STR1157##                                                                        30   185  --  198-207/0.05                                                                          70.25                                                                               70.52                                                                               9.36                                                                                8.98                                                                              3.27 3.04                1407                                                                                      ##STR1158##                                                                        30   185  --  201-211/0.07                                                                          70.25                                                                               70.54                                                                               9.36                                                                                9.12                                                                              3.27 3.03                1408                                                                                      ##STR1159##                                                                        42   185  --  207-211/0.05                                                                          73.61                                                                               73.89                                                                              10.30                                                                               10.08                                                                              3.43 3.15                1409                                                                                      ##STR1160##                                                                        38   185  --  200-214/0.04                                                                          73.61                                                                               73.80                                                                              10.30                                                                               10.17                                                                              3.43 3.11                1410                                                                                      ##STR1161##                                                                        40   180  --  203-213/0.04                                                                          80.90                                                                               81.15                                                                              11.88                                                                               11.59                                                                              3.37 3.16                1411                                                                                      ##STR1162##                                                                        39   185  --  210-223/0.03                                                                          80.15                                                                               80.46                                                                              11.49                                                                               11.10                                                                              3.90 3.65                1412                                                                                      ##STR1163##                                                                        40   185  --  207-217/0.06                                                                          80.15                                                                               80.35                                                                              11.49                                                                               11.31                                                                              3.90 3.74                1413                                                                                      ##STR1164##                                                                        60   185  --  200-210/0.05                                                                          78.27                                                                               78.44                                                                              12.84                                                                               12.63                                                                              4.15 4.07                1414                                                                                      ##STR1165##                                                                        60   200  --  200-213/0.05                                                                          78.56                                                                               78.72                                                                              12.90                                                                               12.74                                                                              3.98 3.82                1415                                                                                      ##STR1166##                                                                        60   200  --  199-209/0.05                                                                          78.84                                                                               79.05                                                                              12.96                                                                               12.81                                                                              3.83 3.71                1416                                                                                      ##STR1167##                                                                        60   200  --  203-215/0.05                                                                          74.73                                                                               74.93                                                                              12.26                                                                               12.05                                                                              3.96 3.85                1417                                                                                      ##STR1168##                                                                        30   185  --  200-214/0.05                                                                          80.37                                                                               80.67                                                                              11.60                                                                               11.40                                                                              3.75 3.63                1418                                                                                      ##STR1169##                                                                        32   185  --  201-207/0.04                                                                          80.56                                                                               80.74                                                                              11.70                                                                               11.57                                                                              3.61 3.61                1419                                                                                      ##STR1170##                                                                        33   200  --  203-211/0.05                                                                          81.14                                                                               81.48                                                                              11.35                                                                               11.25                                                                              3.51 3.58                1420                                                                                      ##STR1171##                                                                        30   185  --  200-215/0.08                                                                          80.56                                                                               80.99                                                                              11.70                                                                               11.53                                                                              3.61 3.49                1421                                                                                      ##STR1172##                                                                        25   200  --  207-223/0.1                                                                           80.56                                                                               80.81                                                                              11.70                                                                               11.46                                                                              3.61 3.44                1422                                                                                      ##STR1173##                                                                        25   185  --  205-213/0.08                                                                          77.07                                                                               77.24                                                                              11.13                                                                               11.02                                                                              3.60 3.43                1423                                                                                      ##STR1174##                                                                        25   185  --  206-223/0.07                                                                          77.07                                                                               77.27                                                                              11.13                                                                               10.96                                                                              3.60 3.25                1424                                                                                      ##STR1175##                                                                        28   190  --  203-222/0.05                                                                          77.36                                                                               77.52                                                                              11.24                                                                               11.01                                                                              3.47 3.39                1425                                                                                      ##STR1176##                                                                        28   190  --  207-219/0.07                                                                          77.36                                                                               77.68                                                                              11.24                                                                               11.04                                                                              3.47 3.28                1426      NH.sub.2 C.sub.12 H.sub.25                                                          33   190  --         80.11                                                                               80.41                                                                              13.22                                                                               13.10                                                                              3.11 3.06                1427                                                                                      ##STR1177##                                                                        30   185  --  218-228/0.06                                                                          80.51                                                                               80.78                                                                              12.31                                                                               12.00                                                                              3.35 3.17                1428                                                                                      ##STR1178##                                                                        60   200  --  210-221/0.04                                                                          80.47                                                                               80.63                                                                              12.83                                                                               13.18                                                                              3.13 3.02                __________________________________________________________________________

EXAMPLE 1429

A mixture of 10 g. of methyl isostearate and 5 g. of cyclohexylamine was stirred at 140° C for 30 hours removing methanol out of the reaction system. The reaction mixture was distilled to obtain 12.1 g. of a desired product, b.p. 200°-205° C./mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       78.84          79.12                                               H (%)       12.96          12.61                                               N (%)       3.83           3.70                                                ______________________________________                                    

EXAMPLE 1430

To a mixture of 10 g. of methyl isostearate and 2 g. of isopropylamine was added a solution of 0.5 g. of sodium in 5 ml. of anhydrous methanol, and the mixture was reacted in an autoclave at 140° C. for 2 hours. The reaction mixture was charged with 100 ml. of ether and washed with water, 5% hydrochloric acid water and water, and was then dried, concentrated and distilled to obtain 9.9 g. of a desired product, b.p. 185°-199° C./0.02 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       77.48          77.64                                               H (%)       13.32          13.10                                               N (%)       4.30           4.19                                                ______________________________________                                    

EXAMPLE 1431

A mixture of 10 g. of methyl isostearate, 2 g of allylamine and 0.5 g. of powdery sodium methylate was stirred in an autoclave at 150° C. for 3 hours. The mixture was treated in the same manner as in Example 1430 to obtain 9.3 g. of a desired product, b.p. 191°-197° C./0.05 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       77.95          77.69                                               H (%)       12.77          12.49                                               N (%)       4.33           4.41                                                ______________________________________                                    

EXAMPLE 1432

A mixture of 10 g. of ethyl isostearate, 6 g. of α-methylbenzylamine and 1 g. of potassium t-butyrate was heated with stirring at 180° C. for 5 hours. Immediately after the heating, the mixture was distilled to obtain 11.8 g. of a desired product, b.p. 205°-208° C./0.1 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.56          80.81                                               H (%)       11.70          11.38                                               N (%)       3.61           3.31                                                ______________________________________                                    

EXAMPLE 1433

A mixture of 10 g. of methyl isostearate and 5 g. of p-methoxy-cyclohexylamine was heated with stirring in an autoclave at 220° C. for 8 hours to obtain 10.4 g. of a desired product, b.p. 204°-211° C./0.05 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       75.89          76.10                                               H (%)       12.48          12.27                                               N (%)       3.54           3.29                                                ______________________________________                                    

EXAMPLE 1434

A mixture of 10 g. of methyl isostearate, 6 g. of cycloheptylamine and 0.5 g. of sodium methylate, and the mixture was heated with stirring at 150° C. for 48 hours removing methanol. Subsequently, the same treatments as in Example 1430 were effected to obtain a desired product, b.p. 206°-210° C.0.09 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       79.09          79.33                                               H (%)       13.01          12.84                                               N (%)       3.69           3.35                                                ______________________________________                                    

EXAMPLE 1435

To a mixture of 10 g. of methyl isostearate and 5 g. of o-toluidine was added a solution of 1 g. of sodium in 10 ml. of anhydrous methanol, and the mixture was stirred at 150° C. for 6 hours, removing methanol. The same treatments as in Example 1430 were effected to obtain a desired product, b.p. 204°-212° C./0.07 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.37          80.57                                               H (%)       11.60          11.29                                               N (%)       3.75           3.50                                                ______________________________________                                    

EXAMPLE 1436

To a mixture of 10 g. of methyl isostearate and 5 g. of 2-chloro-6-methylaniline was added a suspension of 1 g. of sodium methylate in 5 ml. of benzene, and the mixture was stirred at 85° C. for 10 hours. The same treatments as in Example 1430 were effected to obtain 12.1 g. of a desired product, b.p. 209°-215° C./0.06 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       73.61          73.88                                               H (%)       10.30          10.14                                               N (%)       3.43           3.16                                                ______________________________________                                    

EXAMPLE 1437

A mixture of 10 g. of methyl isostearate and 10 g. of dodecylamine, was stirred at 180° C. for 26 hours. The reaction product was treated in the same manner as in Example 1430 to obtain a desired product. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.11          80.41                                               H (%)       13.22          12.89                                               N (%)       3.11           3.01                                                ______________________________________                                    

Examples 1438-1476 are shown in the following table:

    __________________________________________________________________________                                  Reac-                                                                          tion Reac-                                                         Refer-                                                                               Condens-                                                                             temper-                                                                             tion                                         Example          ence  ing   ature                                                                               time                                                                               Sol-                                                                               Auto-                                                                              b.p.                             No.  Amine       example                                                                              agent ° C.                                                                         hr. vent                                                                               clave                                                                              ° C./mmHg                 __________________________________________________________________________     1438                                                                                 ##STR1179##                                                                               1433  --    200  18  --  Used                                                                               189-194/0.04                     1439 NH(CH.sub.2 CHCH.sub.2).sub.2                                                              1433  --    200  18  --  Used                                                                               195-201/0.06                     1440                                                                                 ##STR1180##                                                                               1433  --    200  10  --  Used                                                                               200-204/0.07                     1441                                                                                 ##STR1181##                                                                               1434  NaOCH.sub.3                                                                          150   6  --  --  202-208/0.05                     1442                                                                                 ##STR1182##                                                                               1434  NaOCH.sub.3                                                                          150   6  --  --  200-211/0.05                     1443                                                                                 ##STR1183##                                                                               1434  NaOCH.sub.3                                                                          150   6  --  --  203-213/0.05                     1444                                                                                 ##STR1184##                                                                               1433  --    200  10  --  Used                                                                               205-215/0.05                     1445                                                                                 ##STR1185##                                                                               1429  --    160  30  --  --  209-214/0.04                     1446                                                                                 ##STR1186##                                                                               1429  --    160  35  --  --  208-214/0.04                     1447                                                                                 ##STR1187##                                                                               1429  --    140  60  --  --  198-206/0.04                     1448                                                                                 ##STR1188##                                                                               1429  --    140  58  --  --  202-216/0.04                     1449                                                                                 ##STR1189##                                                                               1434  NaOMe 150   8  --  --  208-214/0.04                     1450                                                                                 ##STR1190##                                                                               1434  NaOMe 150   8  --  --  200-206/0.04                     1451                                                                                 ##STR1191##                                                                               1432  KOtBu 150   8  --  --  200-209/0.04                     1452                                                                                 ##STR1192##                                                                               1431  NaOMe 200  10  --  Used                                                                               204-209/0.04                     1453                                                                                 ##STR1193##                                                                               1431  NaOEt 200  10  --  Used                                                                               200-207/0.06                     1454                                                                                 ##STR1194##                                                                               1431  NaOEt 200  10  --  Used                                                                               200-206/0.06                     1455                                                                                 ##STR1195##                                                                               1431  KOtBu 200  10  --  Used                                                                               209-213/0.05                     1456                                                                                 ##STR1196##                                                                               1431  KOtBu 200  10  --  Used                                                                               206-211/0.07                     1457                                                                                 ##STR1197##                                                                               1435  NaOEt 180   8  MeOH                                                                               --  201-209/0.05                     1458                                                                                 ##STR1198##                                                                               1429  --    180  32  --  --  201-205/0.04                     1459                                                                                 ##STR1199##                                                                               1432  KOtBu 180   5  --  --  203-206/0.05                     1460                                                                                 ##STR1200##                                                                               1429  --    180  20  --  --  211-218/0.04                     1461                                                                                 ##STR1201##                                                                               1429  --    180  20  --  --  209-217/0.04                     1462                                                                                 ##STR1202##                                                                               1429  --    180  22  --  --  208-215/0.05                     1463                                                                                 ##STR1203##                                                                               1429  --    180  20  --  --  205-213/0.04                     1464                                                                                 ##STR1204##                                                                               1433  --    200  20  --  Used                                                                               204-209/0.04                     1465                                                                                 ##STR1205##                                                                               1434  NaOEt 180   5  --  --  200-211/0.07                     1466                                                                                 ##STR1206##                                                                               1434  NaOMe 180   5  --  --  203-217/0.1                      1467                                                                                 ##STR1207##                                                                               1434  NaOMEe                                                                               180   5  --  --  205-212/0.05                     1468                                                                                 ##STR1208##                                                                               1431  NaOMe 200   5  --  Used                                                                               201-206/0.06                     1469                                                                                 ##STR1209##                                                                               1429  --    180  25  --  --  207-220/0.07                     1470                                                                                 ##STR1210##                                                                               1429  --    180  35  --  --  201-207/0.06                     1471                                                                                 ##STR1211##                                                                               1429  --    180  35  --  --  200-209/0.06                     1472                                                                                 ##STR1212##                                                                               1433  --    200  27  --  Used                                                                               209-215/0.06                     1473                                                                                 ##STR1213##                                                                               1433  --    200  30  --  Used                                                                               205-210/0.07                     1474                                                                                 ##STR1214##                                                                               1429  --    180  32  --  --  202-208/0.06                     1475                                                                                 ##STR1215##                                                                               1429  --    200  40  --  --  218-225/0.07                     1476                                                                                 ##STR1216##                                                                               1431  KOtBu 220  10  --  Used                                                                               210-221/0.05                     __________________________________________________________________________                      C %         H %         N %                                                    Theo- Ana-  Theo- Ana-  Theo- Ana-                            Example          reti- lyti- reti- lyti- reti- lyti-                           No.  Amine       cal   cal   cal   cal   cal   cal                             __________________________________________________________________________     1438                                                                                 ##STR1217##                                                                               77.10 77.41 13.27 13.00 4.50  4.31                            1439 NH(CH.sub.2 CHCH.sub.2).sub.2                                                              79.27 79.59 12.47 12.09 3.85  3.55                            1440                                                                                 ##STR1218##                                                                               78.56 78.78 12.90 12.62 3.98  3.78                            1441                                                                                 ##STR1219##                                                                               79.09 79.38 13.01 12.87 3.69  3.48                            1442                                                                                 ##STR1220##                                                                               75.89 75.99 12.48 12.29 3.54  3.23                            1443                                                                                 ##STR1221##                                                                               76.22 76.56 12.55 12.31 3.42  3.19                            1444                                                                                 ##STR1222##                                                                               80.90 81.20 11.88 11.65 3.37  3.17                            1445                                                                                 ##STR1223##                                                                               80.15 80.42 11.49 11.19 3.90  3.65                            1446                                                                                 ##STR1224##                                                                               73.61 73.90 10.30 10.05 3.43  3.33                            1447                                                                                 ##STR1225##                                                                               76.39 76.66 10.61 10.45 3.71  3.70                            1448                                                                                 ##STR1226##                                                                               70.25 70.50 9.36  9.18  3.27  3.29                            1449                                                                                 ##STR1227##                                                                               77.07 77.19 11.13 11.05 3.63  3.85                            1450                                                                                 ##STR1228##                                                                               77.07 77.23 11.13 11.54 3.60  3.32                            1451                                                                                 ##STR1229##                                                                               77.36 77.59 11.24 11.04 3.47  3.34                            1452                                                                                 ##STR1230##                                                                               77.36 77.58 11.24 11.60 3.47  3.21                            1453                                                                                 ##STR1231##                                                                               78.27 78.59 12.84 12.53 4.15  4.00                            1454                                                                                 ##STR1232##                                                                               78.56 78.39 12.90 13.06 3.98  4.05                            1455                                                                                 ##STR1233##                                                                               74.73 74.99 12.26 12.01 3.96  3.80                            1456                                                                                 ##STR1234##                                                                               78.84 79.08 12.96 12.70 3.83  3.62                            1457                                                                                 ##STR1235##                                                                               80.37 80.66 11.60 11.27 3.75  3.65                            1458                                                                                 ##STR1236##                                                                               80.56 80.98 11.70 11.53 3.61  3.47                            1459                                                                                 ##STR1237##                                                                               81.14 81.51 11.35 10.99 3.51  3.31                            1460                                                                                 ##STR1238##                                                                               77.07 77.16 11.13 11.02 3.60  3.48                            1461                                                                                 ##STR1239##                                                                               77.07 77.26 11.13 11.02 3.60  3.50                            1462                                                                                 ##STR1240##                                                                               77.36 77.67 11.24 11.09 3.47  3.13                            1463                                                                                 ##STR1241##                                                                               77.36 77.74 11.24 11.08 3.47  3.21                            1464                                                                                 ##STR1242##                                                                               77.36 77.62 11.24 11.12 3.47  3.19                            1465                                                                                 ##STR1243##                                                                               80.56 80.78 11.70 11.54 3.61  3.58                            1466                                                                                 ##STR1244##                                                                               80.56 80.81 11.70 11.37 3.61  3.51                            1467                                                                                 ##STR1245##                                                                               80.56 80.80 11.70 11.61 3.61  3.60                            1468                                                                                 ##STR1246##                                                                               75.89 76.06 12.48 12.09 3.54  3.41                            1469                                                                                 ##STR1247##                                                                               70.25 70.82 9.36  9.04  3.27  3.00                            1470                                                                                 ##STR1248##                                                                               73.18 73.89 10.16 9.85  3.55  3.19                            1471                                                                                 ##STR1249##                                                                               73.61 73.91 10.30 9.94  3.43  3.18                            1472                                                                                 ##STR1250##                                                                               77.07 77.21 11.13 10.97 3.60  3.30                            1473                                                                                 ##STR1251##                                                                               77.07 77.25 11.13 10.89 3.60  3.41                            1474                                                                                 ##STR1252##                                                                               75.53 75.69 12.41 12.19 3.67  3.33                            1475                                                                                 ##STR1253##                                                                               80.51 80.88 12.31 12.06 3.35  3.16                            1476                                                                                 ##STR1254##                                                                               80.47 80.61 12.83 12.66 3.13  3.04                            __________________________________________________________________________

EXAMPLE 1477

Linoleic acid (16 g.), 16 g. of dicyclohexyl carbodiimide and 9.5 g. of dicyclohexylamine were individually dissolved in 20 ml. of benzene. The thus prepared three solutions were mixed together at one portion, and the mixed solution was stirred for about 3 minutes. The mixed solution was allowed to stand at room temperature for about 18 hours, and 3 ml. of acetic acid was added to the solution, and then the mixture was allowed to stand at room temperature for additional 2 hours. Thereafter, precipitated dicyclohexylurea was separated by filtration, and the filtrate was washed with 5% HCl water, 5% NaOH water and water, and was then dried, concentrated and distilled to obtain 19.2 g. of a desired product, b.p. 200°-209° C./0.05 mmHg, n_(D) ²⁶ 1.4880. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.20          79.94                                               H (%)       12.04          12.00                                               N (%)       3.16           3.24                                                ______________________________________                                    

Examples 1478-1504 are shown in the following table:

    __________________________________________________________________________                                      C (%)     H (%)     N (%)                     Example      Condensing   b.p.   Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-               No.  Acid    agent Solvent                                                                               ° C/mmHg                                                                       tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                __________________________________________________________________________     1478 Linoleic acid                                                                           ##STR1255##                                                                         Dioxane                                                                               203-210/0.07                                                                          81.20                                                                               81.09                                                                               12.04                                                                               11.99                                                                               3.16 3.21                 1479 "                                                                                       ##STR1256##                                                                         Pyridine                                                                              200-208/0.06                                                                          81.20                                                                               81.11                                                                               12.04                                                                               11.98                                                                               3.16 3.19                 1480 "                                                                                       ##STR1257##                                                                         Chloroform                                                                            202-209/0.06                                                                          81.20                                                                               81.07                                                                               12.04                                                                               12.01                                                                               3.16 3.14                 1481 "                                                                                       ##STR1258##                                                                         Chloroform                                                                            203-209/0.06                                                                          81.20                                                                               81.05                                                                               12.04                                                                               12.31                                                                               3.16 3.20                 1482 "                                                                                       ##STR1259##                                                                         Toluene                                                                               201-209/0.06                                                                          81.20                                                                               81.00                                                                               12.04                                                                               11.89                                                                               3.16 3.23                 1483 "                                                                         i-Pro                                                                               Dioxane 201-209/0.05                                                                         81.20  81.14  12.04                                                                               11.95                                                                               3.16 3.18                           1484 "                                                                         i-Pro                                                                               Ether   201-208/0.07                                                                         81.20  81.30  12.04                                                                               12.00                                                                               3.16 3.21                           1485 "                                                                         i-Pro                                                                               Benzene 204-211/0.08                                                                         81.20  80.99  12.04                                                                               12.03                                                                               3.16 3.19                           1486 Linolenic acid                                                                          ##STR1260##                                                                         Dioxane                                                                               204-208/0.06                                                                          81.57                                                                               81.33                                                                               11.64                                                                               11.88                                                                               3.17 3.09                 1487 "                                                                                       ##STR1261##                                                                         Tetrahydro- furan                                                                     200-212/0.07                                                                          81.57                                                                               81.41                                                                               11.64                                                                               11.53                                                                               3.17 3.06                 1488 "                                                                         i-Pro                                                                               Pyridine                                                                               209-215/0.1                                                                          81.57  81.45  11.64                                                                               11.51                                                                               3.17 3.14                           1489 Oleic acid                                                                              ##STR1262##                                                                         Benzene                                                                               195-208/0.05                                                                          80.83                                                                               80.81                                                                               12.44                                                                               12.29                                                                               3.14 3.05                 1490 Safflower oil                                                                           ##STR1263##                                                                         Benzene                                                                               195-213/0.07                                                                          --   --   --   --   --   --                   1491 Cottonseed oil fatty acid                                                               ##STR1264##                                                                         Toluene                                                                               200-214/0.05                                                                          --   --   --   --   --   --                   1492 Cuttlefish oil- fatty acid                                                             "     Ether  200-215/0.05                                                                          --   --   --   --   --   --                   1493 Mackeral oil - fatty acid                                                              "     Tetrahydro- furan                                                                     201-217/0.06                                                                          --   --   --   --   --   --                   1494 Flatfish oil - fatty acid                                                              "     Ether  200-209/0.05                                                                          --   --   --   --   --   --                   1495 Saury pike oil - fatty acid                                                            "     Ether  192-210/0.06                                                                          --   --   --   --   --   --                   1496 Herring oil - fatty acid                                                               "     Tetrahydro- furan                                                                     199-213/0.06                                                                          --   --   --   --   --   --                   1497 Cod oil - fatty acid                                                                   "     Toluene                                                                               187-208/0.04                                                                          --   --   --   --   --   --                   1498 Sardine oil - fatty acid                                                               "     Dioxane                                                                               187-209/0.05                                                                          --   --   --   --   --   --                   1499 Shark oil - fatty acid                                                                 "     Ether  187-211/0.07                                                                          --   --   --   --   --   --                   1500 Liver oil - fatty acid                                                                 "     Dioxane                                                                               200-214/0.06                                                                          --   --   --   --   --   --                   1501 Residual oil - fatty acid                                                              "     Toluene                                                                               205-216/0.08                                                                          --   --   --   --   --   --                   1502 Whale oil - fatty acid                                                                 "     Ether  200-209/0.07                                                                          --   --   --   --   --   --                   1503 Saurel oil - fatty acid                                                                "     Chloroform                                                                            185-211/0.06                                                                          --   --   --   --   --   --                   1504 Menuke oil -                                                                           "     Ether  195-209/0.07                                                                          --   --   --   --   --   --                        fatty acid                                                                __________________________________________________________________________

EXAMPLE 1505

A solution of 16 g. of linoleic acid, 9.5 g. of dicyclohexylamine and 0.5 g. of p-toluenesulfonic acid in 100 ml. of toluene was reacted for 8 hours using a water separator. The reaction product was washed with 5% NaOH water, 5% HCl water and water, and was then dried and concentrated, and the residue was distilled to obtain 18.6 g. of a desired product, b.p. 205°-208° C./0.06 mmHg, n_(D) ²⁵ 1.4882. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.20          79.99                                               H (%)       12.04          11.95                                               N (%)       3.16           3.31                                                ______________________________________                                    

Examples 1506-1530 are shown in the following table, in which:

Catalytic assistant:

A. p-Toluenesulfonic acid

B. p-Toluenesulfonic acid chloride

C. sulfuric acid

D. phenolsulfonic acid

E. ira-400

f. amberlist-15

Solvent:

a. Toluene

b. Pyridine

c. Benzene

d. Chloroform

e. Xylene

f. Tetrachlorocarbon

    __________________________________________________________________________                              Reac-                                                                          tion       C (%)    H (%)    N (%)                    Example                  time                                                                               b.p.   Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-                                                                             Theore-                                                                             Analy-              No.  Acid       Catalyst                                                                            Solvent                                                                            hr  ° C./mmHg                                                                      tical                                                                               tical                                                                              tical                                                                               tical                                                                              tical                                                                               tical               __________________________________________________________________________     1506 Oleic acid A    a   8   204-210/0.06                                                                          80.83                                                                               80.77                                                                              12.44                                                                               12.39                                                                              3.14 3.09                1507 Oleic acid A    c   8   206-210/0.06                                                                          80.83                                                                               80.69                                                                              12.44                                                                               13.33                                                                              3.14 3.08                1508 Oleic acid C    a   8   200-209/0.06                                                                          80.83                                                                               80.45                                                                              12.44                                                                               12.31                                                                              3.14 3.15                1509 Linoleic acid                                                                             A    a   8   203-207/0.05                                                                          81.20                                                                               81.56                                                                              12.04                                                                               12.01                                                                              3.16 3.33                1510 Linoleic acid                                                                             B    b   20  202-207/0.05                                                                          81.20                                                                               81.45                                                                              12.04                                                                               11.87                                                                              3.16 3.45                1511 Linoleic acid                                                                             C    a   8   203-207/0.06                                                                          81.20                                                                               81.09                                                                              12.04                                                                               11.95                                                                              3.16 3.09                1512 Linoleic acid                                                                             D    a   10  204-209/0.06                                                                          81.20                                                                               81.04                                                                              12.04                                                                               11.98                                                                              3.16 3.08                1513 Linoleic acid                                                                             A    a   8   204-209/0.06                                                                          81.20                                                                               81.29                                                                              12.04                                                                               11.88                                                                              3.16 3.43                1514 Linoleic acid                                                                             A    d   10  200-210/0.06                                                                          81.20                                                                               81.09                                                                              12.04                                                                               11.69                                                                              3.16 3.19                1515 Linolenic acid                                                                            A    c   8   206-209/0.06                                                                          81.57                                                                               81.69                                                                              11.64                                                                               11.45                                                                              3.17 3.09                1516 Linolenic acid                                                                            A    c   8   204-210/0.07                                                                          81.57                                                                               81.50                                                                              11.64                                                                               11.39                                                                              3.17 3.00                1517 Linolenic acid                                                                            B    b   20  203-207/0.06                                                                          81.57                                                                               81.47                                                                              11.64                                                                               11.58                                                                              3.17 3.15                1518 Safflower oil acid                                                                        A    d   10  195-207/0.06                                                                          --   --  --   --  --   --                  1519 Cottonseed oil acid                                                                       D    f   10  198-210/0.06                                                                          --   --  --   --  --   --                  1520 Sesame oil acid                                                                           A    b   15  196-209/0.06                                                                          --   --  --   --  --   --                  1521 Castor oil acid                                                                           B    c   8   191-211/0.05                                                                          --   --  --   --  --   --                  1522 Cuttlefish oil acid                                                                       C    a   12  195-214/0.06                                                                          --   --  --   --  --   --                  1523 Mackerel oil acid                                                                         C    e   12  192-213/0.05                                                                          --   --  --   --  --   --                  1524 Flatfish oil acid                                                                         E    e   10  195-209/0.06                                                                          --   --  --   --  --   --                  1525 Saury pike oil acid                                                                       A    a   8   190-214/0.06                                                                          --   --  --   --  --   --                  1526 Herring oil acid                                                                          C    d   8   192-215/0.06                                                                          --   --  --   --  --   --                  1527 Cod oil acid                                                                              B    b   18  188-216/0.05                                                                          --   --  --   --  --   --                  1528 Sardine oil acid                                                                          B    b   18  189-209/0.04                                                                          --   --  --   --  --   --                  1529 Shark oil acid                                                                            A    b   15  187-216/0.06                                                                          --   --  --   --  --   --                  1530 Whale oil acid                                                                            F    a   20  189-217/0.06                                                                          --   --  --   --  --   --                  __________________________________________________________________________

EXAMPLE 1531

A mixture of 16 g. of linoleic acid and 9.5 g. of dicyclohexylamine was heated at 180° C. for 28 hours. The reaction product was immediately distilled to obtain 18.0 g. of a desired product, b.p. 206°-211° C./0.04 mmHg, n_(D) ²⁸ 1.4880. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       31.20          80.99                                               H (%)       12.04          11.98                                               N (%)       3.16           3.14                                                ______________________________________                                    

EXAMPLE 1532

A mixture of 16 g. of methyl linoleate and 13 g. of dicyclohexylamine was reacted at 200° C. for 100 hours, and methanol was removed by distillation out of the reaction system. The reaction product was immediately distilled to obtain 12.0 g. of a desired product, b.p. 205°-213° C./0.05 mmHg. n_(D) ²⁸ 1.4875. Elmentary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.20          80.97                                               H (%)       12.04          12.00                                               N (%)       3.16           3.08                                                ______________________________________                                    

EXAMPLE 1533

To a solution of 14 g. of linoleic acid and 5.5 g. of triethylamine in 100 cc. of tetrahydrofuran was added, 5.9 g. of ethyl chloroformate dropwise under stirring at -10° to -5° C. The stirring was further continued at -5° C. for additional 20 minutes, and then 9.5 g. of dicyclohexylamine was added dropwise under stirring at -5° C. Treatment is in the same manner as in Example 397. Yield: 16.2 g. b.p. 204°-213° C./0.02 mmHg, n_(D) ²³ 1.4888. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.20          80.98                                               H (%)       12.04          11.98                                               N (%)       3.16           3.18                                                ______________________________________                                    

Examples 1534-1548, carried out according to Examples 1531, 1532 and 1533, are shown in the following table:

    __________________________________________________________________________                             C %       H %       N %                                Example         b.p.    Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-                        No.  Acid       ° C./mmHg                                                                       tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                         __________________________________________________________________________     1534 Oleic acid 200-209/0.06                                                                           80.83                                                                               80.75                                                                               12.44                                                                               12.34                                                                               3.14 3.18                          1535 Linolenic acid                                                                            206-209/0.06                                                                           81.57                                                                               81.67                                                                               11.64                                                                               11.48                                                                               3.17 3.07                          1536 Safflower oil acid                                                                        195-206/0.06                                                                           --   --   --   --   --   --                            1537 Cottonseed oil acid                                                                       198-218/0.06                                                                           --   --   --   --   --   --                            1538 Sesame oil acid                                                                           196-207/0.06                                                                           --   --   --   --   --   --                            1539 Castor oil acid                                                                           191-214/0.05                                                                           --   --   --   --   --   --                            1540 Cuttlefish oil acid                                                                       198-214/0.06                                                                           --   --   --   --   --   --                            1541 Mackerel oil acid                                                                         192-215/0.05                                                                           --   --   --   --   --   --                            1542 Flatfish oil acid                                                                         195-208/0.06                                                                           --   --   --   --   --   --                            1543 Saury pike oil acid                                                                       196-214/0.06                                                                           --   --   --   --   --   --                            1544 Herring oil acid                                                                          192-218/0.06                                                                           --   --   --   --   --   --                            1545 Cod oil acid                                                                              188-215/0.05                                                                           --   --   --   --   --   --                            1546 Sardine oil acid                                                                          189-208/0.04                                                                           --   --   --   --   --   --                            1547 Shark oil acid                                                                            187-215/0.06                                                                           --   --   --   --   --   --                            1548 Whale oil acid                                                                            189-219/0.06                                                                           --   --   --   --   --   --                            __________________________________________________________________________

EXAMPLE 1549

To a mixture of 9.3 g. of dicyclohexylamine, 100 ml. of anhydrous ether and 4 g. of trimethylamine was added a solution of 16 g. of linoleic acid chloride in 20 ml. of anhydrous ether under stirring at 0° - 5° C. The reaction mixture was stirred at room temperature for 2 hours and allowed to stand overnight and boiled for 2 hours. Subsequently, the ether solution was washed with 5% HCl water, 5% NaOH water and water, and dried over anhydrous sodium sulfate and concentrated and distilled to obtain 17 g. of a desired product, b.p. 202°-207° C./0.06 mmHg, n_(D) ²⁵ 1.4878. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.20          79.99                                               H (%)       12.04          12.02                                               N (%)        3.16           3.12                                               ______________________________________                                    

Examples 1550-1568 are shown in the following table:

    __________________________________________________________________________     Example                                                                             Chloride                                                                              Condensing        b.p.                                             No.  Acid   agent    Solvent  ° C./mmHg                                 __________________________________________________________________________     1550 Linoleic                                                                              NaOH     H.sub.2 O                                                                               203-208/0.07                                          acid            Dioxane                                                   1551 "      K.sub.2 CO.sub.3                                                                        Methylisobutyl-                                                                         203-208/0.07                                                          ketone                                                    1552 "      Excess of                                                                               Benzene  200-206/0.08                                                  ##STR1265##                                                       1553 "      Na.sub.2 CO.sub.3                                                                       Acetone  205-210/0.08                                     1554 "      KOH      Toluene  204-209/0.07                                     1555 Safflower                                                                             NaOH     H.sub.2 O-dioxane                                                                       198-210/0.06                                          oil acid                                                                  1556 Linolenic                                                                             NaOH     H.sub.2 O-tetrahydro-                                                                   204-209/0.05                                          acid            furan                                                     1557 "      K.sub.2 CO.sub.3                                                                        Acetone  206-210/0.05                                     1558 Oleic acid                                                                             ##STR1266##                                                                            Benzene  200-206/0.06                                     1559 Cuttlefish                                                                            NaOH     H O-dioxane                                                                             200-215/0.06                                          oil                                                                       1560 Mackeral oil                                                                          NaOH     H.sub.2 O-dioxane                                                                       201-216/0.06                                     1561 Flatfish                                                                              NaOH     H.sub.2 O-dioxane                                                                       200-208/0.03                                          oil                                                                       1562 Saury pike                                                                            NaOH     H.sub.2 O-dioxane                                                                       192-210/0.08                                          oil                                                                       1563 Herring oil                                                                           K.sub.2 CO.sub.3                                                                        Methylisobutyl-                                                                         194-211/0.07                                                          ketone                                                    1564 Cod oil                                                                                ##STR1267##                                                                            Ether    198-214/0.06                                     1565 Sardine oil                                                                            ##STR1268##                                                                            Toluene  200-216/0.05                                     1566 Shark oil                                                                              ##STR1269##                                                                            Dimethylform- amide                                                                     198-217/0.07                                     1567 Liver oil                                                                             NaOH     H.sub.2 O-tetrahydro-                                                                   194-220/0.07                                                          furan                                                     1568 Residual                                                                              NaOH     H.sub.2 O-dioxane                                                                       193-264/0.07                                          oil                                                                       __________________________________________________________________________              C (%)     H (%)     N (%)                                             Example  Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-                                                                              Theore-                                                                             Analy-                                       No.  n.sub.D                                                                            tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                                                                               tical                                        __________________________________________________________________________          25                                                                        1550 1.4878                                                                             81.20                                                                               81.09                                                                               12.04                                                                               12.00                                                                               3.16 3.21                                         1551 1.4878                                                                             81.20                                                                               81.14                                                                               12.04                                                                               12.01                                                                               3.16 3.21                                         1552 1.4875                                                                             81.20                                                                               81.13                                                                               12.04                                                                               12.00                                                                               3.16 3.28                                         1553 1.4877                                                                             81.20                                                                               81.10                                                                               12.04                                                                               12.03                                                                               3.16 3.18                                         1554 1.4878                                                                             81.20                                                                               81.09                                                                               12.04                                                                               12.01                                                                               3.16 3.17                                         1555 1.4865                                                                             --   --   --   --   --   --                                           1556 1.4881                                                                             81.57                                                                               81.39                                                                               11.64                                                                               11.58                                                                               3.17 3.15                                         1557 1.4883                                                                             81.57                                                                               81.45                                                                               11.64                                                                               11.59                                                                               3.17 3.15                                         1558 1.4874                                                                             80.83                                                                               80.80                                                                               12.44                                                                               12.38                                                                               3.14 3.09                                         1559 1.4890                                                                             --   --   --   --   --   --                                           1560 1.4895                                                                             --   --   --   --   --   --                                           1561 1.4896                                                                             --   --   --   --   --   --                                           1562 1.4893                                                                             --   --   --   --   --   --                                           1563 1.4880                                                                             --   --   --   --   --   --                                           1564 1.4782                                                                             --   --   --   --   --   --                                           1565 1.4888                                                                             --   --   --   --   --   --                                           1566 1.4873                                                                             --   --   --   --   --   --                                           1567 1.4869                                                                             --   --   --   --   --   --                                           1568 1.4889                                                                             --   --   --   --   --   --                                           __________________________________________________________________________

EXAMPLE 1569

A mixture of 12 g. of linoleic acid, 10 g. of dicyclohexyl carbodiimide, and 6 g. of adamantylamine in 40 ml. of benzene was allowed to stand overnight at room temperature. The mixture was added 3 ml. of acetic acid and was then filtered. The filtrate was washed with 5% hydrochloric acid water, 5% sodium carbonate water and water and was then dried over anhydrous sodium sulfate, and concentrated and distilled to obtain 15.3 g. of a desired product, b.p. 188°-190° C./0.03 mmHg, n_(D) ³⁰ 1.4888 (Yield 86.9%). Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.29          81.56                                               H (%)       11.45          11.90                                               N (%)        3.39           3.72                                               ______________________________________                                    

EXAMPLE 1570

A mixture of 12 g. of stearic acid, 10 g. of diisopropyl carbodiimide and 6 g. of adamantylamine in 20 ml. of tetrahydrofuran were treated in the same manner as in Example 1569 to obtain 13.9 g. of a desired product, b.p. 188°-184° C./0.03 mmHg, (Yield 79.0%). Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.51          80.88                                               H (%)       12.31          11.95                                               N (%)        3.35           3.48                                               ______________________________________                                    

EXAMPLE 1571

A mixture of 12 g. of oleic acid, 10 g. of diphenyl carbodiimide and 6 g. of adamantylamine in 20 ml. of methyl acetate was treated in the same manner as in Example 1569 to obtain 15.1 g. of a desired product, b.p. 187°-189° C./ 0.03 mmHg. (Yield 85.8%). Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.91          80.52                                               H (%)       12.31          12.66                                               N (%)        3.35           3.70                                               ______________________________________                                    

EXAMPLE 1572

A mixture of 12 g. of linoleic acid, 10 g. of dibenzyl carbodiimide and 6 g. of adamantylamine in 40 ml. of chloroform was treated in the same manner as in Example 1569 to obtain 14.3 g. of a desired product, b.p. 188°-191° C./0.03 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.69          81.99                                               H (%)       11.02          10.94                                               N (%)        3.40           3.65                                               ______________________________________                                    

EXAMPLE 1573

A mixture of 12 g. of a mixed fatty acid obtained by hydrolysis of corn oil, a solution of 10 g. of dicyclohexyl carbodiimide in 20 ml. of benzene and a solution of 6 g. of adamantylamine in 10 ml. of benzene was treated in the same manner as in Example 1569 to obtain 10.8 g. of a desired product, b.p. 180°-196° C./0.03 mmHg.

EXAMPLE 1574

A mixture of 12 g. of a mixed fatty acid obtained by hydrolysis of cod oil, a solution of 10 g. of dicyclohexyl carbodiimide in 20 ml. of tetrahydrofuran and a solution of 6 g. of adamantylamine in 10 ml. of tetrahydrofuran was treated in the same manner as in Example 1569 to obtain 11.2 g. of a desired product, b.p. 176°-199° C./0.03 mmHg.

EXAMPLE 1575

A mixture of 10 g. of linoleic acid, 6 g. of adamantylamine, 2 g. of IRA-400 and 50 ml. of toluene was boiled with stirring for about 8 hours, using a water separator. Subsequently, the mixture was washed with 5% HCl water, 5% Na₂ CO₃ water and water to obtain 4.8 g. of a desired product, b.p. 189°-190° C./0.04 mmHg, n_(D) ²⁴ 1.4892. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.29          81.35                                               H (%)       11.45          11.58                                               N (%)        3.39           3.61                                               ______________________________________                                    

EXAMPLE 1576

A mixture of 10 g. of oleic acid, 6 g. of adamantylamine and 3 g. of p-toluenesulfonic acid chloride was boiled for 4 hours in 20 ml. of pyridine. After removing the solvent, the mixture was washed by acid, alkali and water and was then distilled to obtain 8.0 g. of a desired product, b.p. 188°-192° C./0.03 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.91          81.21                                               H (%)       12.31          12.09                                               N (%)        3.35           3.52                                               ______________________________________                                    

EXAMPLE 1577

A mixture of 5 g. of oleic acid, 3 g. of adamantylamine and a small amount of p-toluenesulfonic acid in 20 ml. of toluene was boiled for 8 hours, using a water separator. The reaction product was washed with acid, alkali and water and was then distilled to obtain 4.7 g. of a desired product, b.p. 188°-191° C./0.03 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.91          81.23                                               H (%)       12.31          12.09                                               N (%)        3.35           3.62                                               ______________________________________                                    

EXAMPLE 1578

A mixture of 10 g. of adamantylamine and linoleic acid was heated in a distilling flask at 200° C. for about 1 hour, and was then distilled to obtain 6 g. of a desired product, b.p. 188°-192° C./0.04 mmHg, n_(D) ²⁴ 1.4892. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.29          81.31                                               H (%)       11.45          11.67                                               N (%)        3.39           3.29                                               ______________________________________                                    

EXAMPLE 1579

A mixture of 8 g. of soybean oil and 3 g. of adamantylamine was heated with stirring at 150° C. for 40 hours in a nitrogen atmosphere and was then distilled to obtain 10 g. of a desired product, b.p. 178°-192° C./0.03 mmHg.

EXAMPLE 1580

A mixture of 8 g. of safflower oil, 3 g. of adamantylamine and 0.6 g. of sodium methoxide was heated at 100° C. for 2 hours. In this case, methanol was distilled off out of the system. The reaction mixture was dissolved in ether, and the solution was washed with 5% HCl water, 5% Na₂ CO₃ and water and was then dried and concentrated to obtain 10 g. of a desired product, b.p. 180°-193° C./0.04 mmHg.

EXAMPLE 1581

A solution of 8 g. of cuttlefish oil, 3 g. of adamantylamine and 0.8 g. of potassium t-butoxide in 50 ml. of benzene was boiled for 2 hours. The reaction mixture was washed with 5% HCl water, 5% Na₂ CO₃ and water and was then dried, concentrated and distilled to obtain 8.3 g. of a desired product, b.p. 172°-202° C./0.04 mmHg.

EXAMPLE 1582

A mixture of 10 g. of linoleic anhydride, 5 g. of adamantylamine and 20 ml. of tetrahydrofuran was allowed to stand overnight. Subsequently, the mixture was washed with acid, alkali and water and was then distilled to obtain 4.2 g. of a desired product, b.p. 188°-190° C./0.03 mmHg, n_(D) ²⁴ 1.4891. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.29          81.40                                               H (%)       11.45          11.59                                               N (%)        3.39           3.38                                               ______________________________________                                    

EXAMPLE 1583

To a mixture of 6 g. adamantylamine, 6 g. of potassium carbonate and 50 ml. of methyl-i-butylketone was added 11 g. of linoleic acid chloride. The mixture was allowed to stand overnight at room temperature, and was then heated with stirring at 50° C. for 2 hours. Subsequently, the reaction mixture was washed with 5% hydrochloric acid water, 5% sodium bicarbonate water and water and was then dried, concentrated and distilled to obtain 13.1 g. of a desired product, b.p. 188°-191° C./0.05 mmHg, n_(D) ²⁴ 1.4892. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.29          81.31                                               H (%)       11.45          11.67                                               N (%)        3.39           3.29                                               ______________________________________                                    

EXAMPLE 1584

Palmitic acid chloride (10 g.) was added dropwise at 2°-5° C. to a solution of 5 g. of adamantylamine and 3.2 g. of pyridine in 50 ml. of benzene. Subsequently, the mixture was treated in the same manner as in Example 1569 to obtain 10.5 g. of a desired product, b.p. 183°-186° C./0.02 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.14          80.40                                               H (%)       12.16          12.09                                               N (%)        3.60           3.47                                               ______________________________________                                    

EXAMPLE 1585

Linoleic acid chloride (10 g.) was added dropwise to a solution of 6 g. of adamantylamine and 2 g. of caustic soda in a water-dioxane. Thereafter, the same treatments as in Example 1569 were effected to obtain 11.2 g. of a desired product. b.p. 188°-192° C./0.03 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.69          81.87                                               H (%)       11.02          10.81                                               N (%)        3.40           3.51                                               ______________________________________                                    

EXAMPLE 1586

Oleic acid chloride (10 g.) was added dropwise to a solution of 5 g. of adamantylamine in 30 ml. of trimethylamine. Thereafter, the same treatments as in Example 1569 were effected to obtain 10.1 g. of a desired product, b.p. 185°-188° C./0.02 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.91          81.05                                               H (%)       12.31          12.19                                               N (%)        3.35           3.41                                               ______________________________________                                    

EXAMPLE 1587

Safflower oil fatty acid chloride (10 g.) was added 5 g. of adamantylamine in the same manner as in Example 1569 to obtain 9.8 g. of a desired product, b.p. 180°-194° C./0.04 mmHg.

EXAMPLE 1588

Sardine oil fatty acid chloride (10 g.) was added to 5 g. of adamantylamine in the same manner as in Example 1569 to obtain 9.3 g. of a desired product, b.p. 164°-208° C./0.05 mmHg.

EXAMPLE 1589

A mixture of 10 g. of t-butyl linoleate and 10 g. of adamantylamine was stirred in a nitrogen atmosphere at 150° C. for 40 hours, and then the mixture was distilled to obtain 13.0 g. of a desired product, b.p. 185°-186° C./0.02 mmHg, n_(D) ³⁰ 1.4889 (Yield 87.8%) Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.29          81.55                                               H (%)       11.45          11.71                                               N (%)        3.39           3.69                                               ______________________________________                                    

EXAMPLE 1590

A mixture of 10 g. of methyl linoleate, 5.5 g. of adamentylamine and 2 g. of sodium methylate was heated with stirring at 100° C. for 1 hour, the methanol was distilled off out of the reaction system. The reaction product was dissolved in ether and the ether layer was washed with water, dried, concentrated and distilled to obtain 13.0 g. of desired product, b.p. 188°-189° C./0.03 mmHg, n_(D) ³² 1.4884 (Yield 87.8%) Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       81.29          81.09                                               H (%)       11.45          11.59                                               N (%)        3.39           3.48                                               ______________________________________                                    

EXAMPLE 1591

A mixture of 10 g. of methyl oleate and 6 g. of adamantylamine were heated with stirring at 140° C. for about 50 hours, and then the mixture was distilled to obtain a desired product, b.p. 188°-192° C./0.03 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.91          81.09                                               H (%)       12.91          12.18                                               N (%)        3.35           3.51                                               ______________________________________                                    

EXAMPLE 1592

A mixture of 10 g. of methyl palmitate, 6 g. of adamentylamine, 50 ml. of benzene and 2 g. of sodium ethylate was refluxed for 2 hours to obtain a desired product, b.p. 182°-186° C./0.03 mmHg. Elementary analysis:

    ______________________________________                                                   Theoretical  Analytical                                              ______________________________________                                         C (%)       80.14          80.31                                               H (%)       12.16          12.05                                               N (%)        3.60           3.51                                               ______________________________________                                    

EXAMPLE 1593

A mixture of 10 g. of safflower oil methyl ester and 6 g. of adamentylamine was heated at 150° C. for 50 hours and was then distilled to obtain 11.2 g. of a desired product, b.p. 177°-199° C./0.03 mmHg.

EXAMPLE 1594

A mixture of 10 g. of ethyl ester of cod oil and 6 g. of adamentylamine was heated at 150° C. for 40 hours to obtain 9.2 g. of a desired product, b.p. 168°-213° C./0.03 mmHg.

    __________________________________________________________________________     Following amides are also synthesized according to the above mentioned         methods.                                                                                                  C %         H %         N %                                             .sup.n D                                                                              Theoretical                                                                          Analytical                                                                           Theoretical                                                                          Analytical                                                                           Theoretical                                                                          Analytical            __________________________________________________________________________      ##STR1270##        23°1.5120                                                                      72.86 72.90 9.41  9.27  6.54  6.44                   ##STR1271##        22°1.5118                                                                      72.86 72.95 9.41  9.22  6.54  6.43                   ##STR1272##        32°1.5123                                                                      72.93 73.12 9.97  10.07 6.30  6.19                   ##STR1273##        33°1.5122                                                                      72.93 73.10 9.97  10.05 6.30  6.15                   ##STR1274##        32°1.5012                                                                      73.60 73.82 9.15  9.28  6.36  6.18                   ##STR1275##        30°1.5020                                                                      73.60 73.76 9.15  9.22  9.36  6.22                   ##STR1276##        27°1.5163                                                                      72.18 72.00 10.25 10.09 6.48  6.52                   ##STR1277##        24°1.5140                                            ##STR1278##        20°1.5142                                            ##STR1279##        21°1.5222                                            ##STR1280##        23°1.5220                                                               b.p.   C %         H %         N %                                             ° C.mmHg.                                                                      Theoretical                                                                          Analysis                                                                             Theoretical                                                                          Analysis                                                                             Theoretical                                                                          Analysis              __________________________________________________________________________      ##STR1281##        214-223°/0.04                                                                  78.40 78.49 10.48 10.66 3.39  3.33                   ##STR1282##        214-224/0.04                                                                          78.40 78.53 10.48 10.68 3.39  3.20                   ##STR1283##        210-221/0.03                                                                          78.02 78.20 10.91 11.05 3.37  3.27                   ##STR1284##        213-223/0.03                                                                          78.02 78.21 10.91 11.16 3.37  3.22                   ##STR1285##        213-225/0.03                                                                          78.02 78.19 10.91 11.09 3.37  3.30                   ##STR1286##        218-228/0.04                                                                          77.64 77.77 11.34 11.50 3.35  3.50                   ##STR1287##        216-228/0.03                                                                          77.64 77.80 11.34 11.48 3.35  3.52                   ##STR1288##        217-225/0.05                                                                          79.61 79.42 10.18 10.12 3.29  3.40                   ##STR1289##        217-227/0.05                                                                          79.61 79.53 10.18 10.20 3.29  3.38                   ##STR1290##        208-227/0.04                                                ##STR1291##        210-227/0.03                                               __________________________________________________________________________

    __________________________________________________________________________                          C %           H %           N %                                                Theoretical                                                                           Analytical                                                                            Theoretical                                                                           Analytical                                                                            Theoretical                                                                           Analytical             __________________________________________________________________________      ##STR1292##   Semi solid                                                                           83.24  83.33  10.26  10.45  3.03   3.31                    ##STR1293##   "     83.24  83.40  10.26  10.39  3.03   2.94                    ##STR1294##   "     83.97  84.01  9.47   9.67   3.06   3.00                    ##STR1295##   "     83.97  84.13  9.47   9.53   3.06   2.99                    ##STR1296##   "     83.97  84.22  9.47   9.57   3.06   3.21                    ##STR1297##   "                                                                ##STR1298##   "                                                               __________________________________________________________________________

    __________________________________________________________________________                                C %         H %         N %                                                    Theoretical                                                                          Analysis                                                                             Theoretical                                                                          Analysis                                                                             Theoretical                                                                          Analysis              __________________________________________________________________________      ##STR1299##       222-236°/0.08                                                                   67.24 67.40 9.05  8.97  3.01  2.78                   ##STR1300##       219-223/0.03                                                                           67.24 67.38 9.05  9.15  3.01  2.84                   ##STR1301##       215-230/0.05                                                                           74.02 74.20 10.43 10.65 3.32  3.19                   ##STR1302##       214-232/0.05                                                                           74.02 74.21 10.43 10.67 3.32  3.30                   ##STR1303##       205-217/0.05                                                                           75.09 75.24 9.14  9.33  3.36  3.29                   ##STR1304##       209-219/0.04                                                                           75.09 75.30 9.14  9.30  3.36  3.28                   ##STR1305##       215-224/0.03                                                 ##STR1306##       213-225/0.03                                                 ##STR1307##       190-232/0.04                                                 ##STR1308##       192-228/0.03                                                __________________________________________________________________________

    __________________________________________________________________________                                C %         H %         N %                                                    Theoretical                                                                          Analytical                                                                           Theoretical                                                                          Analytical                                                                           Theoretical                                                                          Analytical            __________________________________________________________________________      ##STR1309##       200-218/0.05                                                                           81.29 81.43 11.45 11.55 3.39  3.22                   ##STR1310##       200-215/0.05                                                                           81.29 81.50 11.45 11.62 3.39  3.21                   ##STR1311##       198-215/0.06                                                                           80.72 80.91 11.83 12.02 3.49  3.42                   ##STR1312##       196-215/0.06                                                                           80.73 80.88 11.83 12.07 3.49  3.39                   ##STR1313##       210-221/0.04                                                                           81.97 82.14 10.45 10.62 3.54  3.47                   ##STR1314##       209-218/0.04                                                                           81.97 82.13 10.45 10.55 3.54  3.39                   ##STR1315##       200-212°/0.03                                         ##STR1316##       200-214/0.03                                                 ##STR1317##       194-227/0.04                                                 ##STR1318##       190-226/0.04                                                __________________________________________________________________________ 

What is claimed is:
 1. A composition consisting essentially of a cholesterol lowering pharmaceutically effective amount of a compound of the formula, ##EQU2## wherein R is a C₁₃ -C₂₅ aliphatic hydrocarbon chain or a C₁₃ -C₂₅ hydroxylated aliphatic hydrocarbon chain, R' is racemic-, d- or l-α-benzylbenzyl, and R" is hydrogen, and a solid or liquid pharmaceutically acceptable carrier.
 2. A method of lowering cholesterol content in patients having an elevated cholesterol level, which comprises orally administering 0.1 to 20 grams per day of a compound of the formula, ##STR1319## wherein R is a C₁₃ -C₂₅ aliphatic hydrocarbon chain or a C₁₃ -C₂₅ hydroxylated aliphatic hydrocarbon chain, R' racemic-, d- or l-α-benzylbenzyl, and R" is hydrogen. 